N-(2,3-Dihydro-5-nitro-1H-inden-2-yl)-2,2,2-trifluoroacetamide → N-(5-amino-2,3-dihydro-1H-inden-2-yl)-2,2,2-trifluoroacetamide

HRID 1157621Notes

Reaction equation

HRID 1157621 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([NH:5][CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:15]([O-])=O)[CH:12]=2)[CH2:7]1)=[O:4]>CCOC(C)=O.[Pd]>[NH2:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([NH:5][C:3](=[O:4])[C:2]([F:1])([F:18])[F:19])[CH2:14]2

Participants

4

Reactant 1

HCID 16083804N-(2,3-Dihydro-5-nitro-1H-inden-2-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 59511384N-(5-amino-2,3-dihydro-1H-inden-2-yl)-2,2,2-trifluoroacetamideYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2,2,2-Trifluoro-N-(5-nitro-2,3-dihydro-1H-inden-2-yl)acetamide (245 mg, 0.89 mmol) was dissolved in EtOAc and stirred vigorously for 15 h. with 5% Pd/C (70 mg) under hydrogen atmosphere (1 atm). The reaction was filtered through celite and the solvent was removed under vacuum. Filtration yielded 214 mg (98%) of the desired amine as a brown powder. 1H NMR (400 MHz, DMSO-d6) δ 9.60 (d, J=7.1 Hz, 1H), 6.81 (d, J=8.0 Hz, 1H), 6.39 (s, 1H), 6.34 (d, J=8.1 Hz, 1H), 4.83 (s, 2H), 4.43 (m, 1H), 3.01 (m, 2H), 2.71 (m, 2H); ES-LC/MS (M+H)+=245.11.

Workup

  1. filtrationThe reaction was filtered through celite
  2. customthe solvent was removed under vacuum
  3. filtrationFiltration

Sources & evidence

ORD record
ord-ec0cb2c40c924297b256e18b2f0d49b1
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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