(7-Chloro-2-methyl-quinolin-8-yl)-acetic acid tert-butyl ester → (7-Chloro-2-methyl-quinolin-8-yl)-acetic acid ethyl ester

HRID 1968737Notes

Reaction equation

[C:1]([O:5][C:6](=[O:20])[CH2:7][C:8]1[C:9]([Cl:19])=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[C:15]([CH3:18])[CH:14]=[CH:13]2)(C)(C)[CH3:2]>C(O)C.Cl>[CH2:1]([O:5][C:6](=[O:20])[CH2:7][C:8]1[C:9]([Cl:19])=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[C:15]([CH3:18])[CH:14]=[CH:13]2)[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

(7-Chloro-2-methyl-quinolin-8-yl)-acetic acid tert-butyl ester (650 mg, 2.23 mmol) was dissolved in ethanol (13 ml) saturated with HCl gas. The solution was heated to 90° C. for 10 minutes. After cooling, volatiles were removed in vacuo, and the residue was purified via flash chromatography (gradient of hexane:EtOAc 95:5 to 80:20) to afford the title compound (372 mg, 63%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ=8.00 (d, J=8.8 Hz, 1H), 7.66 (d, J=8.8 Hz, 1H), 7.48 (d, J=9.2 Hz, 1H), 7.27 (d, J=8.8 Hz, 1H); 4.52 (s, 2H), 4.19 (q, J=7.3 Hz, 2H), 2.81 (s, 3H), 1.27 (t, J=7.3 Hz, 3H). MS (ES+): 264.2 (M+H)+.

Workup

temperatureAfter cooling
customvolatiles were removed in vacuo
customthe residue was purified via flash chromatography (gradient of hexane:EtOAc 95:5 to 80:20)

Sources & evidence

ORD record: ord-9ac9811b784d4325938b0c9aaa30c203
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426440B2

Reaction notes

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