Hydrazine hydrate (1:1) → HCID 59320372, compound

HRID 655273Notes

Reaction equation

HRID 655273 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[C:9]([F:12])[C:8]([CH2:13][C:14]([OH:16])=O)=[CH:7][CH:6]=2.O.[NH2:18][NH2:19]>CO>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[C:9]([F:12])[C:8]([CH2:13][C:14]([NH:18][NH2:19])=[O:16])=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59320396HCID 59320396, compound

Product 1

HCID 59320372HCID 59320372, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3-bromo-5-fluoro-quinolin-6-yl)-acetic acid (800 mg, 2.7 mmol) and hydrazine hydrate (98%, 2 mL) in methanol (15 mL) was heated to reflux for 1 h. The solvent was removed in vaco to obtain a white solid which was washed with methanol and dried to return the title compound (750 mg, 94%) as a white solid. 1H-NMR (DMSO-d6, 300 MHz): 9.34 (s, 1H), 8.996-9.00 (d, 1H), 8.72-8.73 (d, 1H), 7.85-7.88 (d, 1H), 7.73-7.79 (m, 1H), 4.26-4.27 (d, 2H), 3.64-3.66 (d, 2H); MS: m/z 299 [M+H+]+.

Workup

  1. temperatureto reflux for 1 h
  2. customThe solvent was removed in vaco
  3. customto obtain a white solid which
  4. washwas washed with methanol
  5. customdried

Sources & evidence

ORD record
ord-fc3bfcd10d7644099d59ea10d9f6715c
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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