(7-Methyl-quinolin-6-yl)-acetic acid tert-butyl ester → 2-(7-Methylquinolin-6-yl)acetic acid

HRID 655226Notes

Reaction equation

HRID 655226 reaction equation
C([O:5][C:6](=[O:19])[CH2:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[CH3:18])[N:14]=[CH:13][CH:12]=[CH:11]2)(C)(C)C>[OH-].[Na+]>[CH3:18][C:17]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[N:14]2)=[CH:9][C:8]=1[CH2:7][C:6]([OH:19])=[O:5]

Participants

3

Reactant 1

HCID 68703613(7-Methyl-quinolin-6-yl)-acetic acid tert-butyl ester

Product 1

HCID 593203942-(7-Methylquinolin-6-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

3.2 g of (7-methyl-quinolin-6-yl)-acetic acid tert-butyl ester in 25 ml of aqueous NaOH (4N) was heated to reflux for 4 h. The mixture was washed with ethyl acetate and added concentrated hydrochloric acid to pH 7. A white solid formed which was filtered and dried to return the title compound (1.5 g, 71.1%). 1H NMR (DMSO-d6, 300 MHz) δ 12.46 (s, 1H), 8.82 (m, 1H), 8.26 (m, 1H), 7.82 (s, 1H), 7.77 (s, 1H), 7.44 (m, 1H), 3.80 (s, 2H), 2.44 (s, 3H) ES-MS m/z: 202 (M++H).

Workup

  1. temperatureto reflux for 4 h
  2. washThe mixture was washed with ethyl acetate
  3. additionadded concentrated hydrochloric acid to pH 7
  4. customA white solid formed which
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-047fd60e94b742eea9633d0cab1bf1e9
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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