Ethanol → 2-Amino-2-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-yl)acetic acid hydrochloride

HRID 1769551Notes

Reaction equation

HRID 1769551 reaction equation
[ClH:1].[NH2:2][CH:3]([CH:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:13][CH2:12][C:11]2[CH:20]=[CH:21][CH:22]=[CH:23][C:10]1=2)[C:4]([O:6]CC)=[O:5].[OH-].[K+].C(O)C>O>[ClH:1].[NH2:2][CH:3]([CH:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:13][CH2:12][C:11]2[CH:20]=[CH:21][CH:22]=[CH:23][C:10]1=2)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 19385933Ethyl 2-amino-2-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-yl)acetate hydrochloride

Product 1

HCID 678056032-Amino-2-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-yl)acetic acid hydrochlorideYield 74.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl α-amino-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-acetate hydrochloride (13 g, 39 mmol) is stirred with 400 mL of 1M ethanolic potassium hydroxide solution at room temperature overnight. Ethanol is stripped and the solid taken up in water, extracted with diethyl ether, and acidified with 1N hydrochloric acid to pH 1. A precipitate is collected by filtration, washed with diethyl ether, dried at 50° C./2 mm Hg to furnish 8.81 g of the title compound; mp >285° C.

Workup

  1. extractionextracted with diethyl ether
  2. filtrationA precipitate is collected by filtration
  3. washwashed with diethyl ether
  4. customdried at 50° C./2 mm Hg

Sources & evidence

ORD record
ord-1ec819d9346348c1bd2efef21e72a47f
Source dataset
uspto-grants-1995_01
Patent number
US05380925

Reaction notes

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