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

HRID 1769550Notes

Reaction equation

HRID 1769550 reaction equation
[N+:1]([CH:4]([CH:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH:14]=[CH:13][C:12]2[CH:21]=[CH:22][CH:23]=[CH:24][C:11]1=2)[C:5]([O:7]CC)=[O:6])([O-])=O.O.[ClH:26]>C(O)C.[Pd]>[ClH:26].[NH2:1][CH:4]([CH:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH2:14][CH2:13][C:12]2[CH:21]=[CH:22][CH:23]=[CH:24][C:11]1=2)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 15290760Ethyl alpha-nitro-5H-dibenzo[a,d]cycloheptene-5-acetate

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl α-nitro-5H-dibenzo[a,d]cycloheptene-5-acetate (13 g, 40 mmol) (Example 4, Step A) is dissolved in 150 mL of ethanol, 40 mL of water, and 3.5 mL of concentrated hydrochloric acid and hydrogenated with 2.0 g of 20% palladium on carbon (52 psi, 30 hours). The filtered solution is stripped and a white solid washed with diethyl ether, dried at 50° C./2 mm Hg. The crude product is used as is in the next step.

Workup

  1. washa white solid washed with diethyl ether
  2. customdried at 50° C./2 mm Hg

Sources & evidence

ORD record
ord-ff3351fa33294fdd840bc4be3053edf5
Source dataset
uspto-grants-1995_01
Patent number
US05380925

Reaction notes

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