Synthesis of Lidocaine Lap Report

SYNTHESIS OF LIDOCAINE

OVERALL OBJECTIVES:

Lidocaine will be synthesized in a multistep synthesis beginning with the reduction of 2, 6-dimethylnitrobenzene to 2, 6-dimethylaniline using stannous chloride. This compound will then be purified and used along with α-chloroacetyl chloride to create α-chloro-2,6-dimethylacetanilide. This solid will be reacted with diethylamine to produce the final product, Lidocaine. The final product will be collected and analyzed via melting point determinations, IR, HNMR, C13NMR, DEPT, COSY, and HETCOR.

2, 6-dimethyl-nitrobenzene

2, 6-dimethyl-nitrobenzene

α-chloro-2,6-dimethylacetanilide

α-chloro-2,6-dimethylacetanilide

2, 6-dimethylaniline

2, 6-dimethylaniline

Lidocaine

Lidocaine

PART A: 2, 6-DIMETHYLANILINE

Objective:

Convert 2, 6-dimethylnitrobenzene to 2, 6-dimethylaniline using stannous chloride as the reducing agent. The product extracted using diethyl ether and purified by a water wash. An NMR will be taken to verify that 2, 6-dimethylaniline was produced and to determine purity.

Table of Reagents/Products:

Name | Molecular Weight (g/mol) | Weight/ Volume | Amount Used (mol) | Density (g/mL) | MP (°C) |

Stannous Chloride | 225.63 | 67.70g | 0.3000 | n/a | 37-38 |

Hydrochloric Acid | 36.46 | 120mL | 3.8837 | 1.18 | n/a |

*2,6-dimethylnitrobenzene* | 151.16 | 13.5mL | *0.0993* | 1.112 | n/a |

Glacial acetic acid | 60.05 | 150mL | 2.6203 | 1.049 | n/a |

Water | 18.015 |...