HCID 56993354, compound → HCID 57120211, compound

HRID 1769206Notes

Reaction equation

HRID 1769206 reaction equation
[CH2:1]1[O:21][C:4]([CH2:19][CH3:20])([CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[C:7]=2[N+:16]([O-])=O)[O:3][CH2:2]1>C(O)C.[Pd]>[CH2:2]1[O:3][C:4]([CH2:19][CH3:20])([CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[C:7]=2[NH2:16])[O:21][CH2:1]1

Participants

4

Reactant 1

HCID 56993354HCID 56993354, compound

Product 1

HCID 57120211HCID 57120211, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-(3-methoxycarbonyl-2-nitrophenyl)butan-2-one ethylene ketal (36) (1.12 g) (prepared, e.g., as described in Preparation 24), in absolute ethanol (50 ml) was added palladium on carbon (150 mg, 10%), and the mixture stirred under hydrogen at atmospheric pressure and room temperature for 6 hours. The reaction mixture was passed through a Celite pad to remove catalyst, and the pad was washed with methylene chloride. The combined filtrate and washings were concentrated under reduced pressure to give 1-(2-amino-3-methoxycarbonyl-phenyl)butan-2-one ethylene ketal (0.98 g), a compound of Formula (37), as a colorless oil.

Workup

  1. customto remove catalyst
  2. washthe pad was washed with methylene chloride
  3. concentrationThe combined filtrate and washings were concentrated under reduced pressure

Sources & evidence

ORD record
ord-deaddc74ed114fd7ad7a0eadb2258c31
Source dataset
uspto-grants-1995_01
Patent number
US05380739

Reaction notes

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