HCID 68703923, compound → HCID 59320212, compound

HRID 655235Notes

Reaction equation

HRID 655235 reaction equation
C([O:5][C:6](=[O:19])[CH2:7][C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([CH3:18])[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)(C)(C)C>[OH-].[Na+]>[CH3:18][C:16]1[CH:17]=[C:8]([CH2:7][C:6]([OH:19])=[O:5])[CH:9]=[C:10]2[C:15]=1[N:14]=[CH:13][CH:12]=[CH:11]2

Participants

3

Reactant 1

HCID 68703923HCID 68703923, compound

Product 1

HCID 59320212HCID 59320212, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

3.5 g of (8-methyl-quinolin-6-yl)-acetic acid tert-butyl ester in 18 ml of NaOH (4N, aq.) was heated to reflux for 3 h. The mixture was washed with ethyl acetate and the water layer was acidified with 1N hydrochloric acid to pH 4-5 and extracted with dichloromethanfe. The solvent was evaporated and the resulting solid was washed with water and dried in vacuo to return the title compound as an off white solid (1.3 g, 48%). 1H NMR (DMSO-d6, 300 MHz) δ 12.42 (s, 1H), 8.90 (m, 1H), 8.30 (m, 1H), 7.66 (s, 1H), 7.54 (m, 2H), 3.74 (s, 2H), 2.70 (s, 3H).

Workup

  1. temperatureto reflux for 3 h
  2. washThe mixture was washed with ethyl acetate
  3. extractionextracted with dichloromethanfe
  4. customThe solvent was evaporated
  5. washthe resulting solid was washed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-85a33368492743e8ad18f366267ce834
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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