HCID 66965897, compound → HCID 66966120, compound

HRID 1514918Notes

Reaction equation

HRID 1514918 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:24])[C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]([NH:20][CH2:21][CH2:22][OH:23])[CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]>CO.[Pd]>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]([NH:9][C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=2)=[O:24])=[CH:12][C:13]=1[NH:20][CH2:21][CH2:22][OH:23]

Participants

4

Reactant 1

HCID 66965897HCID 66965897, compound

Product 1

HCID 66966120HCID 66966120, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(3,4-dimethyl-phenyl)-3-(2-hydroxyethylamino)-4-nitro-benzamide (70 mg) in MeOH (20 mL) was added 10% Pd/C (10 mg). The reaction mixture was stirred under H2 balloon at room temperature for 16 h. The reaction mixture was filtered through celite, washed with MeOH. The filtrate was concentrated under reduced pressure to give 4-amino-N-(3,4-dimethyl-phenyl)-3-(2-hydroxy-ethylamino)-benzamide as a grey solid; MS (m/z) 300 (M+1); 1H NMR (DMSO-d6, 400 MHz) δ 9.54 (s, 1H), 7.51 (s, 1H), 7.45 (d, 1H), 7.18 (d, 1H), 7.04 (d, 2H), 6.57 (d, 1H), 5.12 (s, 2H), 4.69 (t, 1H), 4.50 (t, 1H), 3.65 (q, 2H), 3.19 (q, 2H), 2.20 (s, 3H), 2.17 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bef8e8909d004f5bb3a11748418a2cf9
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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