Hydrazine hydrate (1:1) → HCID 178487706, compound

HRID 2405837Notes

Reaction equation

HRID 2405837 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][C:9]([O:16][CH3:17])=[CH:10][CH:11]=2)[N:6]=1)=O.O.[NH2:19][NH2:20]>CO>[OH:15][C:13]1[C:12]2[C:7](=[CH:8][C:9]([O:16][CH3:17])=[CH:10][CH:11]=2)[N:6]=[C:5]([C:3]([NH:19][NH2:20])=[O:2])[CH:14]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178498512HCID 178498512, compound

Product 1

HCID 178487706HCID 178487706, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-hydroxy-7-methoxy-quinoline-2-carboxylic acid methyl ester (2.0 g, 8.58 mmol) in methanol (85 mL) was added hydrazine mono hydrate (1.7 g, 34.3 mmol) and the mixture was refluxed for 6 hours. The crude reaction mixture was concentrated in vacuo and the residue was taken up in methanol and poured onto an ice/water mixture (800 mL). A white precipitate formed, which was collected by filtration and washed with cold water. The filter cake was then dried on house vacuum by passing air through in sintered glass funnel, and then dried on vacuum oven at 45° C. overnight to afford 4-hydroxy-7-methoxy-quinoline-2-carboxylic acid hydrazide (1.6 g, 80% yield). 1H NMR (DMSO-d6, 300 MHz) δ 11.57 (s, 1H), 10.28 (s, 1H), 7.95 (d, 1H), 7.43 (d, 1H), 7.01-6.91 (m, 1H), 6.54 (s, 1H), 4.72 (br s, 2H), 3.82 (s, 3H). LCMS found 234.18 [M+H]+.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo
  4. additionpoured onto an ice/water mixture (800 mL)
  5. customA white precipitate formed
  6. filtrationwhich was collected by filtration
  7. washwashed with cold water
  8. customThe filter cake was then dried on house vacuum
  9. customdried on vacuum oven at 45° C. overnight

Sources & evidence

ORD record
ord-73994e74d428418c8921bc2bfc33d874
Source dataset
uspto-grants-2014_08
Patent number
US08809267B2

Reaction notes

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