Hydrochloric Acid → 3-Fluoro-4-hydroxybenzohydrazide

HRID 1589724Notes

Reaction equation

HRID 1589724 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5](OC)=[O:6].O.[NH2:14][NH2:15].Cl>O>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([NH:14][NH2:15])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 7019368Methyl 3-fluoro-4-hydroxybenzoate

Product 1

HCID 109099793-Fluoro-4-hydroxybenzohydrazideYield 92.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

10.00 g (58.8 mM) of methyl 3-fluoro-4-hydroxybenzoate and 17.5 ml of 80%-hydrazine hydrate were mixed and stirred for 1 hour and 20 minutes at 100° C., followed by cooling to room temperature. The resultant mixture was poured into 150 ml of iced water and 16.8 ml of concentrated hydrochloric acid was added thereto (pH=about 8), followed by addition of common salt and stirring at room temperature to precipitate a crystal. The crystal was recovered by filtration and stirred in methanol at room temperature. The resultant crystal was recovered from the above mixture by filtration to obtain 9.26 g of 3-fluoro-4-hydroxybenzohydrazide (Yield: 92.6%).

Workup

  1. temperatureby cooling to room temperature
  2. additionwas added
  3. addition(pH=about 8), followed by addition of common salt
  4. stirringstirring at room temperature
  5. customto precipitate a crystal
  6. filtrationThe crystal was recovered by filtration
  7. stirringstirred in methanol at room temperature
  8. filtrationThe resultant crystal was recovered from the above mixture by filtration

Sources & evidence

ORD record
ord-99973426cf554ef1ab6281d583d9f09c
Source dataset
uspto-grants-1993_04
Patent number
US05200109

Reaction notes

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