Formic Acid → HCID 20394975, compound

HRID 261447Notes

Reaction equation

HRID 261447 reaction equation
[C:1]([C:5]1[C:15]2[CH2:14][CH2:13][NH:12][CH2:11][CH:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]=2[CH:8]=[C:7]([O:22][CH3:23])[C:6]=1[O:24][CH3:25])([O:3][CH3:4])=[O:2].[OH-].[Na+].[CH:28](O)=O>C=O>[C:1]([C:5]1[C:15]2[CH2:14][CH2:13][N:12]([CH3:28])[CH2:11][CH:10]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:9]=2[CH:8]=[C:7]([O:22][CH3:23])[C:6]=1[O:24][CH3:25])([O:3][CH3:4])=[O:2]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 20394958HCID 20394958, compound

Product 1

HCID 20394975HCID 20394975, compound

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Procedure

A solution of 3.7 g of 6-carbomethoxy-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-carbomethoxy-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-53de1ef3bff94857ab450b8d2865bad1
Source dataset
uspto-grants-1979_08
Patent number
US04165372

Reaction notes

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