Hydrazine hydrate (1:1) → HCID 59320259, compound

HRID 655274Notes

Reaction equation

HRID 655274 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]([CH3:15])[C:12](O)=[O:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.O.[NH2:17][NH2:18]>CO>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]([CH3:15])[C:12]([NH:17][NH2:18])=[O:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 190360062-(Quinolin-6-yl)propanoic acid

Product 1

HCID 59320259HCID 59320259, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Quinolin-6-yl-propionic acid (5.6 g, 26.1 mmol), hydrazine hydrate (1.6 mL) and methanol (150 mL) were combined and heated to reflux for 72 hours. After such time the mixture was concentrated in vacuo and portioned between NaHCO3 (200 mL) and dichloromethane (150 mL). The aqueous phase was extracted with dichloromethane (2×150 mL) and the combined organic extracts dried (Na2SO4) and concentrated in vacuo to return the title compound as a white solid (4.6 g, 21.4 mmol, 82%). 1H-NMR (DMSO-d6, 500 MHz): 9.30 (1H, bs), 8.85 (1H, dd), 8.33 (1H, dd), 7.95 (1H, d), 7.86 (1H, d), 7.74 (1H, dd), 7.51 (1H, dd), 4.22 (3H, s), 3.74 (1H, q), 1.44 (3H; MS: m/z 216 [M+H+]+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 72 hours
  3. concentrationAfter such time the mixture was concentrated in vacuo
  4. extractionThe aqueous phase was extracted with dichloromethane (2×150 mL)
  5. dry with materialthe combined organic extracts dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f9a25ea9b4cc47ef90c7f351661b4849
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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