Hydrazine → 3-Morpholin-4-yl-benzoic acid hydrazide

HRID 1777035Notes

Reaction equation

HRID 1777035 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10](OC)=[O:11])[CH2:3][CH2:2]1.[NH2:17][NH2:18]>CO>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([NH:17][NH2:18])=[O:11])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 7148402Methyl 3-(morpholin-4-yl)benzoate

Product 1

HCID 71483853-Morpholin-4-yl-benzoic acid hydrazideYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Methyl 3-morpholinobenzoate (100 mg, 0.452 mmol) was added to hydrazine (14.48 mg, 0.452 mmol) in methanol (10 mL) and refluxed for 12 h at 65° C. The reaction was monitored by TLC. Upon completion of the reaction and following cooling, the solvent was removed by vacuum and the compound was purified by column chromatography (2% CH3OH/CH2Cl2) affording the title compound as a solid (52 mg). 1H NMR (400 MHz, DMSO-d6): δ 9.69 (s, 1H), 7.35 (s, 1H), 7.27 (m, 2H), 7.07 (m, 1H), 4.45 (bs, 2H), 3.74 (m, 4H), 3.14 (m, 4H). ESI-MS: 222.1 [M+H]+.

Workup

  1. customUpon completion of the reaction
  2. temperaturefollowing cooling
  3. customthe solvent was removed by vacuum
  4. customthe compound was purified by column chromatography (2% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-f82320589535403698db3362d845d979
Source dataset
uspto-grants-2016_02
Patent number
US09266838B2

Reaction notes

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