Acetic Anhydride → HCID 13392483, compound

HRID 2413114Notes

Reaction equation

HRID 2413114 reaction equation
[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][NH:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([N:9]1[CH2:8][CH2:7][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[C:12]=2[CH2:11][CH2:10]1)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 117762SK&F 101055

Product 1

HCID 13392483HCID 13392483, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1.5 g. of 6-chloro-2,3,4,5-tetrahydro-1H-3-benzazepine, 2.0 g. of acetic anhydride and 20 ml. of pyridine was stirred at room temperature for 3 hours. The mixture was concentrated in vacuo and the residue washed with 3N hydrochloric acid, then water, to yield 3-acetyl-6-chloro-2,3,4,5-tetrahydro-1H-3-benzazepine melting at 64°-66°. This amide was reduced in ether with a 50% excess of lithium aluminum hydride at reflux for 6 hours. Upon decomposition of excess reducing agent, the reaction mixture was filtered and the ethereal filtrate dried over magnesium sulfate. The filtrate was treated with ethereal hydrogen chloride solution to precipitate 6-chloro-3-ethyl-2,3,4,5-tetrahydro-1H -3-benzazepine as the hydrochloride salt which melted at 274°-275° from absolute alcohol.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. washthe residue washed with 3N hydrochloric acid

Sources & evidence

ORD record
ord-b933615b58a44dfd9d3e292e8eb5f96b
Source dataset
uspto-grants-1985_01
Patent number
US04496558

Reaction notes

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