7-Nitro-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid ethyl ester → 7-Amino-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid ethyl ester

HRID 925230Notes

Reaction equation

HRID 925230 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=[CH:16][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]>CCOC(C)=O>[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[C:14]([NH2:17])[CH:15]=[CH:16][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 584953837-Nitro-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid ethyl ester

Product 1

HCID 584948787-Amino-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid ethyl esterYield 85.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into a Parr hydrogenation bottle, the product from step (a) (17 g) dissolved in EtOAc (200 ml) was added. To the Ar purged bottle 10% Pd—C (1.7 g) was added. The reaction mixture was shaken under hydrogen (50 psi) for 3 hours. The reaction mixture was filtered through celite and solvent evaporated in vacuo to give the sub-title compound as an off-white solid (12.9 g). 1H NMR (300 MHz, CDCl3) δ 6.77 (d, J=7.8 Hz, 1H); 6.35 (s, 1H); 6.30 (d, J=8.1 Hz, 1H); 4.84 (s, 2H); 4.06 (q, J=6.9 Hz, 2H); 3.43 (bs, 4H); 2.66 (bs, 4H); 1.19 (t, 7.2 Hz, 3H). MS: ESI (positive): 235 (M+H).

Workup

  1. additionwas added
  2. customTo the Ar purged bottle 10% Pd—C (1.7 g)
  3. additionwas added
  4. filtrationThe reaction mixture was filtered through celite and solvent
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-a213ffe7a8864e0eb7721ab15250e7d3
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

Loading…