Isoniazid → HCID 73223071, compound

HRID 882698Notes

Reaction equation

HRID 882698 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[B:9]1[O:17][C:14]([CH3:16])([CH3:15])[C:11]([CH3:13])([CH3:12])[O:10]1)=O.[C:18]([NH:26][NH2:27])(=[O:25])[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1>C([O-])(=O)C.[Na+]>[CH3:12][C:11]1([CH3:13])[C:14]([CH3:16])([CH3:15])[O:17][B:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH:1]=[N:27][NH:26][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[O:10]1

Participants

4

Reactant 2

HCID 3767IsoniazidHCID 109773222-Formylphenylboronic acid pinacol ester

Product 1

HCID 73223071HCID 73223071, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 517045Sodium AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A portion of (2-formylphenyl)boronic acid pinacol ester (1 mmol, 0.232 g) was added to a nearly saturated solution of isonicotinic acid hydrazide (1 mmol, 0.137 g) in 0.1 M pH 4.5 sodium acetate buffer. The reaction mixture was stirred over an oil bath at 100° C. in for 4 min. The white insoluble product was collected via vacuum filtration, washed with water, and dried in vacuo to give an off-white powder in 67% yield. Recrystallization by slow evaporation of CH2Cl2 or vapor diffusion of CH2Cl2 and hexanes afforded translucent plates suitable for X-ray diffraction. 1H NMR (DMSO): δ 1.341 (12H, s), 7.447 (2H, td, J=1.20, J=6.47), 7.565 (1H, t, J=7.07), 7.736 (1H, d, J=6.72), 7.818 (2H, dd, J=1.47, J=4.49), 8.029 (1H, d, J=7.68), 8.791 (2H, d, J=5.8), 8.963 (1H, s), 12.20 (1H, s); 13C NMR (DMSO): δ 62.07, 121.45, 138.27, 159.21, 163.11, 166.70, 168.59, 173.04, 176.79, 186.85, 187.74, 187.89; MS (ESI): m/z 352.3 (M+H+), 374.3 (M+Na+), 350.1 (M−H+); IR (neat, cm−1): 3179, 3059, 2974, 1643, 1550, 1479, 1346, 1292, 1141. 1056; UV-vis (MeOH) nm (M−1 cm−1): 208 (20,320), 302 (19,530).

Workup

  1. filtrationThe white insoluble product was collected via vacuum filtration
  2. washwashed with water
  3. customdried in vacuo
  4. customto give an off-white powder in 67% yield
  5. customRecrystallization
  6. customby slow evaporation of CH2Cl2 or vapor diffusion of CH2Cl2 and hexanes afforded translucent plates suitable for X-ray diffraction

Sources & evidence

ORD record
ord-9fcb9319a6e94e55b0766097bedb1923
Source dataset
uspto-grants-2012_08
Patent number
US08236783B2

Reaction notes

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