N,N-Dimethyl-5-nitro-2-indanamine → (5-amino-2,3-dihydro-1H-inden-2-yl)dimethylamine

HRID 1157619Notes

Reaction equation

HRID 1157619 reaction equation
[CH3:1][N:2]([CH3:15])[CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:12]([O-])=O)[CH:9]=2)[CH2:4]1.[H][H]>CO.[Pd]>[NH2:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH2:4][CH:3]([N:2]([CH3:15])[CH3:1])[CH2:11]2

Participants

5

Reactant 2

HCID 25138868N,N-Dimethyl-5-nitro-2-indanamineHCID 178418361HCID 178418361, compound

Product 1

HCID 54309634(5-amino-2,3-dihydro-1H-inden-2-yl)dimethylamineYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dimethyl(5-nitro-2,3-dihydro-1H-inden-2-yl)amine (1.5 g, 7.3 mmol)) was dissolved in MeOH and stirred vigorously with of 5% Pd/C (250 mg) under a 55 PSI atmosphere of hydrogen for 15 h. The reaction was filtered through celite and the solvent was removed under vacuum. The reaction produced 1.2 g (94%) of the white powder (5-amino-2,3-dihydro-1H-inden-2-yl)dimethylamine. 1H NMR (400 MHz, DMSO-d6) δ 6.84 (d, J=8.2 Hz, 1H), 6.41 (s, 1H), 6.38-6.36 (m, 1H), 4.88 (s, 2H), 3.86 (quint, J=8.8 Hz, 1H), 3.16-2.88 (m, 4H), 2.60 (s, 6H).

Workup

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

Sources & evidence

ORD record
ord-0ec291ecdb7a48069cf438b60d19c7c9
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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