2-Hydrazinobenzoic acid → HCID 136389265, compound

HRID 1927275Notes

Reaction equation

HRID 1927275 reaction equation
[NH:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O)[NH2:2].O=[CH:13][CH:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:15]#[N:16]>C(O)(=O)C>[C:17]1([C:14]2[CH:13]=[N:2][N:1]3[C:3]4[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=4)[C:5](=[O:7])[NH:16][C:15]=23)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 792232-Hydrazinobenzoic acidHCID 3458802-Formyl-2-phenylacetonitrile

Product 1

HCID 136389265HCID 136389265, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-hydrazinobenzoic acid (0.15 g, 0.8 mmol) and 3-oxo-2-phenyl-propionitrile (0.116 g, 0.8 mmol) in acetic acid (0.2 mL) was heated in a microwave (Personal Chemistry SmithSynthesizer) at 150° C. for 10 minutes. The precipitated product was filtered, washed with methanol and diethyl ether and dried. 1H NMR (DMSO-d6) δ 12.10 (s, 1H), 8.10-8.19 (m, 3H) 7.88-7.96 (m, 1H), 7.59 (d, J=7.3 Hz, 2H), 7.52 (t, J=7.8 Hz, 1H), 7.42 (t, J=7.6 Hz, 2 Hz), 7.28 (t, J=7.3 Hz, 1H).

Workup

  1. filtrationThe precipitated product was filtered
  2. washwashed with methanol and diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-1baab54997a8455b95ca3e859df7362f
Source dataset
uspto-grants-2012_05
Patent number
US08183250B2

Reaction notes

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