Isoniazid → HCID 76808974, compound

HRID 449306Notes

Reaction equation

HRID 449306 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18]([C:21](=O)[CH3:22])=[CH:19][CH:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:24]([NH:32][NH2:33])(=[O:31])[C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1>C(O)C>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18]([C:21](=[N:33][NH:32][C:24](=[O:31])[C:25]5[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=5)[CH3:22])=[CH:19][CH:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 3767IsoniazidHCID 58514909HCID 58514909, compound

Product 1

HCID 76808974HCID 76808974, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of example 208 (0.065 g, 0.214 mmol) in ethanol (1.5 ml), isonicotinic hydrazide (0.050 g, 0.428 mmol) was added refluxed for 12 h. The reaction mixture was concentrated and the residue was washed with water, ethyl acetate and dried under vacuum to afford the title compound as a single isomer and as a pale yellow solid (0.070 g, 77%). M.P.: 239-241° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 11.24 (s, 1H), 8.88 (dd, J=4.1, 2.5 Hz, 1H), 8.77 (s, 2H), 8.60 (br s, 1H), 8.37 (d, J=8.0 Hz, 2H), 8.02 (d, J=8.8 Hz, 2H), 7.82 (d, J=7.1 Hz, 2H), 7.71 (m, 1H), 7.54 (dd, J=8.3, 4.2 Hz, 1H), 6.18 (s, 2H), 2.55 (s, 3H).

Workup

  1. temperaturerefluxed for 12 h
  2. concentrationThe reaction mixture was concentrated
  3. washthe residue was washed with water, ethyl acetate
  4. customdried under vacuum

Sources & evidence

ORD record
ord-6633f06b7dc045728922cb263f2a304a
Source dataset
uspto-grants-2013_07
Patent number
US08481739B2

Reaction notes

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