Hydrazine hydrate (1:1) → 4-(3-Bromo-benzyloxy)-2-hydroxy-benzoic acid hydrazide

HRID 18436Notes

Reaction equation

HRID 18436 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[C:9]([OH:16])[CH:8]=1.O.[NH2:21][NH2:22]>CO.C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([NH:21][NH2:22])=[O:12])=[C:9]([OH:16])[CH:8]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 100418444-(3-Bromo-benzyloxy)-2-hydroxy-benzoic acid

Product 1

HCID 102464394-(3-Bromo-benzyloxy)-2-hydroxy-benzoic acid hydrazideYield 16.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

A slurry of 4-(3-bromo-benzyloxy)-2-hydroxy-benzoic acid (2.15 g; 6.4 mmol) in MeOH (10 mL) was added hydrazine hydrate (3 mL; 62 mmol) and heated to 120° C. in a sealed metal cylinder for 40 min. The cylinder was cooled on ice and the slurry diluted with THF in order to dissolve precipitate. The clear solution was evaporated onto SiO2, and purified by filtration through a plug of Silica gel (SiO2—PE80-100° C./EtOAc=4:1; EtOAc then EtOAc/CH2Cl2=3:2) to yield after evaporation 0.9 g (42%). The compound was further purified by crystallization from MeOH/THF to yield 350 mg pure product. Mp. 201-203° C.; MS (ESI−): 335/337 (MH−).

Workup

  1. temperatureThe cylinder was cooled on ice
  2. dissolutionto dissolve precipitate
  3. customThe clear solution was evaporated onto SiO2
  4. filtrationpurified by filtration through a plug of Silica gel (SiO2—PE80-100° C
  5. customEtOAc then EtOAc/CH2Cl2=3:2) to yield
  6. customafter evaporation 0.9 g (42%)
  7. customThe compound was further purified by crystallization from MeOH/THF

Sources & evidence

ORD record
ord-4459535b605c4aa38ac04e36d72a93c7
Source dataset
uspto-grants-2010_06
Patent number
US07741352B2

Reaction notes

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