Water → 2-(4-Hydroxyphenyl)acetohydrazide

HRID 1244631Notes

Reaction equation

HRID 1244631 reaction equation
F[C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C:7]2[O:11]C(N)=[N:9][N:8]=2)=[CH:4][CH:3]=1.NN.[OH2:17]>>[OH:17][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C:7]([NH:8][NH2:9])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 219193195-[(4-Fluorophenyl)methyl]-1,3,4-oxadiazol-2-amine

Product 1

HCID 37318662-(4-Hydroxyphenyl)acetohydrazide

Conditions

Temperature
195 °C

Procedure

A mixture of 5-(4-fluoro-benzyl)-[1,3,4]oxadiazol-2-ylamine 10.182 g (52.7 mmol), water 80 mL and anhydrous hydrazine 20 mL was refluxed under nitrogen on an oil bath (190-200 ° C.) for 23 hours. The mixture was cooled and allowed to crystallize at R.T. under nitrogen overnight. The precipitated product was collected by filtration, washed with ice-cold water (10 mL) and dried on high vacuum. The crude product was re-crystallized from water 60 mL (reflux under nitrogen, than to +4° C. in a refrigerator overnight). The product was filtered, washed with ice-cold water and dried on high vacuum. Y=6.210 g (56.5%) of a large white crystals. 1H-NMR(DMSO-d6, 400 MHz): 7.267 (app d, J=8.6 Hz, J=5.5 Hz, 2H), 7.097 (app t, J=9.0 Hz, 2H), 5.509 (br s, 2H), 5.339 (s, 2H), 3.884 (s, 2H); 19F-NMR(DMSO-d6, 376.5 MHz): −117.14 (m, 1F).

Workup

  1. temperatureThe mixture was cooled
  2. customto crystallize at R.T. under nitrogen overnight
  3. filtrationThe precipitated product was collected by filtration
  4. washwashed with ice-cold water (10 mL)
  5. customdried on high vacuum
  6. customThe crude product was re-crystallized from water 60 mL (
  7. temperaturereflux under nitrogen, than to +4° C. in a refrigerator overnight)
  8. filtrationThe product was filtered
  9. washwashed with ice-cold water
  10. customdried on high vacuum

Sources & evidence

ORD record
ord-fd1dbd1458d24080953c1352bc7faab9
Source dataset
uspto-grants-2006_10
Patent number
US07122548B2

Reaction notes

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