Formic Acid → 6-Chloro-2,3,4,5-tetrahydro-7,8-dimethoxy-3-methyl-1-phenyl-1H-3-benzazepine

HRID 1701327Notes

Reaction equation

HRID 1701327 reaction equation
[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][NH:9][CH2:8][CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:5]=[C:4]([O:19][CH3:20])[C:3]=1[O:21][CH3:22].[OH-].[Na+].[CH:25](O)=O>C=O>[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([CH3:25])[CH2:8][CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:5]=[C:4]([O:19][CH3:20])[C:3]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 12668015HCID 12668015, compound

Product 1

HCID 4359706-Chloro-2,3,4,5-tetrahydro-7,8-dimethoxy-3-methyl-1-phenyl-1H-3-benzazepine

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Procedure

A solution of 3.7 g of 6-chloro-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine in 15 ml of formic acid and 10 ml of formaldehyde is refluxed for 18 hours. The reaction mixture is evaporated to dryness, 20 ml of 6N hydrochloric acid is added and the solution is again evaporated to dryness to give a liquid. The latter is treated with 20 ml of 10% sodium hydroxide solution and the mixture is extracted with ether. The dried extract is evaporated to give 6-chloro-7,8-dimethoxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine.

Workup

  1. customThe reaction mixture is evaporated to dryness, 20 ml of 6N hydrochloric acid
  2. additionis added
  3. customthe solution is again evaporated to dryness
  4. customto give a liquid
  5. extractionthe mixture is extracted with ether
  6. extractionThe dried extract
  7. customis evaporated

Sources & evidence

ORD record
ord-5154528ae85946a28920a08e17436ef8
Source dataset
uspto-grants-1980_03
Patent number
US04192872

Reaction notes

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