Water → 4-(3-Hydrazino-3-oxopropyl)benzohydrazide

HRID 642093Notes

Reaction equation

HRID 642093 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10](OC)=[O:11])=[CH:8][CH:7]=1.O.[NH2:18][NH2:19].O.[NH:21](C(=O)CCC1C=C(C=CC=1)C(OC)=O)[NH2:22]>CO>[NH:18]([C:3](=[O:2])[CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([NH:21][NH2:22])=[O:11])=[CH:8][CH:7]=1)[NH2:19]

Participants

6

Reactant 4

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 595759Methyl 4-(3-methoxy-3-oxopropyl)benzoateHCID 68411053Methyl 3-(3-hydrazino-3-oxopropyl)benzoate

Product 1

HCID 684097474-(3-Hydrazino-3-oxopropyl)benzohydrazideYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of methyl 4-(3-methoxy-3-oxopropyl)benzoate (500 mg, 2.25 mmol) in MeOH (10 mL) was added hydrazine hydrate (1.09 mL). After stirring for 18 h at rt, the reaction mixture was poured into water (30 mL). The solvent was evaporated off until a final volume of 5 mL and a white solid precipitated out. Filtration and drying under vacuo at 70° C. overnight gave a white solid which was identified as methyl 3-(3-hydrazino-3-oxopropyl)benzoate (38 mg, 8%) [1H NMR (300 MHz, DMSO-d6) δ 8.95 (s, 1H), 7.85 (d, J=7.9 Hz, 2H), 7.33 (d, J=7.9 Hz, 2H), 4.17 (s, 2H), 3.82 (s, 3H), 2.87 (t, J=7.7 Hz, 2H), 2.33 (t, J=7.7 Hz, 2H)]. And the filtrate was evaporated off under vacuo. The white residue was washed with MeOH and dryed under vacuo at 70° C. overnight to give 4-(3-hydrazino-3-oxopropyl)benzohydrazide (278 mg, 56%) [1H NMR (300 MHz, DMSO-d6) δ 9.66 (s, 1H), 8.94 (s, 1H), 7.71 (d, J=8.3 Hz, 2H), 7.25 (d, J=8.3 Hz, 2H), 4.43 (s, 2H), 4.14 (s, 2H), 2;84 (t, J=7.8 Hz, 2H), 2.32 (t, J=7.8 Hz, 2H)].

Workup

  1. customThe solvent was evaporated off until a final volume of 5 mL
  2. customa white solid precipitated out
  3. filtrationFiltration
  4. customdrying under vacuo at 70° C. overnight
  5. customgave a white solid which
  6. customAnd the filtrate was evaporated off under vacuo
  7. washThe white residue was washed with MeOH
  8. waitdryed under vacuo at 70° C. overnight

Sources & evidence

ORD record
ord-5a0d4accdcfe429b924a5e05f098de00
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

Loading…