Water → HCID 136349838, compound

HRID 1399490Notes

Reaction equation

HRID 1399490 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:3]=1[CH:4]=O.[Cl:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([NH:18][NH2:19])=[O:17])=[CH:14][CH:13]=1.O>CCO>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:3]=1[CH:4]=[N:19][NH:18][C:16](=[O:17])[C:15]1[CH:14]=[CH:13][C:12]([Cl:11])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 108164-ChlorobenzohydrazideHCID 5283932-Chloro-6-hydroxybenzaldehyde

Product 1

HCID 136349838HCID 136349838, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 2-chloro-6-hydroxybenzaldehyde (0.10 g, 0.64 mmol) and 4-chlorobenzoic acid hydrazide (0.10 g, 0.61 mmol) in EtOH (3 mL) was agitated and heated to 60° C. for 16 h. The reaction mixture was cooled to room temperature and H2O (1-2 mL) was added portionwise to precipitate the product. The solid was collected via suction filtration and rinsed with ethanol to furnish the title compound as an off-white solid (0.18 g, 95%): mp 273-277° C.; 1H NMR (400 MHz, DMSO-d6) δ 12.53 (s, 1H), 12.51 (s, 1H), 9.04 (s, 1H), 8.03-7.95 (m, 2H), 7.71-7.63 (m, 2H), 7.34 (t, J=8.2 Hz, 1H), 7.07 (dd, J=7.9, 0.9 Hz, 1H), 6.96 (d, J=8.2 Hz, 1H); ESIMS m/z 309 ([M+H]+), 307 ([M−H]−).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customto precipitate the product
  3. filtrationThe solid was collected via suction filtration
  4. washrinsed with ethanol

Sources & evidence

ORD record
ord-e487fd582c8e4239be999a432eefdcf0
Source dataset
uspto-grants-2014_12
Patent number
US08906829B2

Reaction notes

Loading…