Ethanol → HCID 67263999, compound

HRID 1687350Notes

Reaction equation

HRID 1687350 reaction equation
C(OC([N:11]1[CH2:17][C:16]2[CH:18]=[C:19]([O:25][CH3:26])[C:20]([N+:22]([O-])=O)=[CH:21][C:15]=2[N:14]([CH2:27][CH3:28])[C:13](=[O:29])[CH2:12]1)=O)C1C=CC=CC=1.C(O)C>[Pd]>[NH2:22][C:20]1[C:19]([O:25][CH3:26])=[CH:18][C:16]2[CH2:17][NH:11][CH2:12][C:13](=[O:29])[N:14]([CH2:27][CH3:28])[C:15]=2[CH:21]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 67263639HCID 67263639, compound

Product 1

HCID 67263999HCID 67263999, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 1-Ethyl-7-methoxy-8-nitro-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid benzyl ester (0.95 g, 0.0024 mol). and 10% Pd/C (10:90, Palladium:carbon black, 0.095 g) in Ethanol (100 mL, 2 mol) was hydrogenated on a Paar shaker for 1 day. The catalyst was filtered and the filtrate evaporated to give 8-Amino-1-ethyl-7-methoxy-1,3,4,5-tetrahydro-benzo-[e][1,4]diazepin-2-one as a tan solid (0.55 g). (98%). Mp 69-73° C.; LCMS (m/e) 236 (M+1); 1H-NMR (DMSO, 400 MHz) δ 6.75 (s, 1H), 6.61 (s, 1H), 4.83 (s, 2H), 3.76 (s, 3H), 3.74-68 (q, 2H, J=7.33 Hz), 3.58 (s, 2H), 2.97 (s, 2H), 1.05-02 (t, 3H, J=7.32 Hz).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-a96ce07a324c47c79a8b3233b8f8f017
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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