Ethanone, 1-(2,3-dihydro-5-nitro-1H-indol-1-yl)- → 1-(5-amino-2,3-dihydro-1H-indol-1-yl)ethan-1-one

HRID 373723

Reaction equation

HRID 373723 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-])=O)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[H][H]>[Pd].C(OCC)(=O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH2:13])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 36566Ethanone, 1-(2,3-dihydro-5-nitro-1H-indol-1-yl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 2925071-(5-amino-2,3-dihydro-1H-indol-1-yl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Palladium on carbon (10%, 1.110 g) is added to a mixture of N-acetyl-5-nitro indoline (II, EXAMPLE 1, 5.00 g) in ethyl acetate (freshly opened bottle, about 500 ml). The mixture is stirred under 1 atm of hydrogen (balloon) for 39 hr then filtered and the palladium on carbon is washed with methanol/ethyl acetate (20/80). The filtrate is concentrated under reduced pressure to give the title compound, mp 183°-185°; NMR (CDCl3, 300 MHz) 8.01, 6.53, 6.50, 3.98, 3.56, 3.04 and 2.17 δ; CMR (CDCl3, 75.47 MHz) 23.86, 28.05, 48.71, 111.55, 113.73, 117.66, 132.8, 135.6, 149.1 and 168.1 δ; IR (CHCl3) 3000, 1640, 1600, 1490, 1410, 1330 and 1300 cm-1.

Workup

  1. filtrationthen filtered
  2. washthe palladium on carbon is washed with methanol/ethyl acetate (20/80)
  3. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-78d03da115ea44fb893a94fede8427ef
Source dataset
uspto-grants-1992_11
Patent number
US05164510

Linked notes

Loading…