Hydrochloric Acid → alpha-Acetylamino-10,11-dihydro-5H dibenzo[a,d]cycloheptene-5-acetic acid

HRID 2399633Notes

Reaction equation

HRID 2399633 reaction equation
Cl.[NH2:2][CH:3]([CH:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][CH2:10][C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]1=2)[C:4]([OH:6])=[O:5].[C:22](OC(=O)C)(=[O:24])[CH3:23].Cl>[OH-].[Na+].O>[C:22]([NH:2][CH:3]([CH:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][CH2:10][C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]1=2)[C:4]([OH:6])=[O:5])(=[O:24])[CH3:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 678056032-Amino-2-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-yl)acetic acid hydrochloride

Product 1

HCID 19385928alpha-Acetylamino-10,11-dihydro-5H dibenzo[a,d]cycloheptene-5-acetic acidYield 47.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

α-Amino-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-acetic acid, hydrochloride (5.0 g, 16.5 mmol) is dissolved in 1N sodium hydroxide (70 mL) and 50 mL of water, cooled in an ice bath, and treated with acetic anhydride (2.3 mL, 25 mmol) keeping pH at 10 to 10.5. The mixture is stirred for an additional 20 minutes, then the pH is adjusted to 3 to 4 with concentrated hydrochloric acid. A precipitate is collected, washed with water, diethyl ether, and dried in a vacuum oven (50° C./10 mm Hg). The dried solid is recrystallized from ethyl acetate-hexane to give 2.41 g of the title compound; mp 220°-223° C.

Workup

  1. customA precipitate is collected
  2. washwashed with water, diethyl ether
  3. customdried in a vacuum oven (50° C./10 mm Hg)
  4. customThe dried solid is recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-43edf79a78bc4ff3a61aae6769708ff5
Source dataset
uspto-grants-1995_09
Patent number
US05449778

Reaction notes

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