Hydrochloric Acid → Ethyl 2-amino-2-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-yl)acetate hydrochloride

HRID 258196Notes

Reaction equation

HRID 258196 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][CH2:8][CH3:9])=[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]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 3

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

Product 1

HCID 19385933Ethyl 2-amino-2-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-yl)acetate 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-60d4a1eac74e4c15ab2aa7f26df34e18
Source dataset
uspto-grants-1993_11
Patent number
US05264577

Reaction notes

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