Hydrochloric Acid → 1-Acetyl-7-hydroxy-2,3,4,5-tetrahydro-1H-benzazepine

HRID 1741044Notes

Reaction equation

HRID 1741044 reaction equation
C([O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:14]([C:15](=[O:17])[CH3:16])[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:18]=1)(=O)C.[OH-].[Na+].Cl>C(O)C.O>[C:15]([N:14]1[C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:18][C:9]=2[CH2:10][CH2:11][CH2:12][CH2:13]1)(=[O:17])[CH3:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 218337947-Acetoxy-1-acetyl-2,3,4,5-tetrahydro-1H-benzazepine

Product 1

HCID 218338251-Acetyl-7-hydroxy-2,3,4,5-tetrahydro-1H-benzazepineYield 63%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

7-Acetoxy-1-acetyl-2,3,4,5-tetrahydro-1H-benzazepine (D23, 3.88 g, 16 mmol) was stirred in ethanol (40 ml) as NaOH (1.26 g, 32 mmol) was added in water (5 ml). After stirring for 30 min, the mixture was diluted with water (500 ml), and acidified with 5M HCl. The tan precipitate was filtered off and dried, yielding 2.02 g (63%) of the title compound. A further 0.80 g (25%) of this material was isolated by dichloromethane extraction of the filtrate.

Workup

  1. filtrationThe tan precipitate was filtered off
  2. customdried

Sources & evidence

ORD record
ord-b8ad193304a448c9b19819e47a0f6ce6
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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