HCID 67263496, compound → HCID 67264040, compound

HRID 1687249Notes

Reaction equation

HRID 1687249 reaction equation
[CH3:1][N:2]1[C:8]2[C:9]([N+:13]([O-])=O)=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=[O:16])[N:5]([CH3:17])[CH2:4][CH2:3]1>CO.[Pd]>[NH2:13][C:9]1[C:8]2[N:2]([CH3:1])[CH2:3][CH2:4][N:5]([CH3:17])[C:6](=[O:16])[C:7]=2[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 67263496HCID 67263496, compound

Product 1

HCID 67264040HCID 67264040, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1,4-Dimethyl-9-nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (#) (300 mg, 1.27 mmol) was dissolved in MeOH (20 ml) and placed in a Parr bottle. Pd—C (10%, 30 mg) was added, and the resulting mixture was shaken under 20 psi H2 for 2 h. The reaction mixture was filtered through celite, washed with MeOH, and concentrated to afford 9-Amino-1,4-dimethyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one as a light grey solid (253 mg, 99%). mp 165-166° C.; LCMS: m/z=206.29 (M+H+), 1H NMR (400 MHz, CDCl3) δ 7.06 (m, 2H), 6.86 (m, 1H), 3.34 (m, 4H), 3.19 (s, 3H), 2.79 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with MeOH
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-01ab910151684986b596d182d8b2ff23
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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