Hydrochloric Acid → 4-(quinolin-2-ylmethoxy)benzoic Acid

HRID 33820

반응식

HRID 33820 반응식
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)=[CH:6][CH:5]=1.[OH-].[Na+].Cl>O1CCCC1.CO.[Cl-].[Na+].O>[N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][C:12]=1[CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:22])=[O:2])=[CH:5][CH:6]=1

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19934817Methyl 4-(2-quinolinylmethoxy)benzoate

생성물 1

HCID 98385524-(quinolin-2-ylmethoxy)benzoic Acid수율 98%

시약·촉매·용매 3

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of 4-(Quinolin-2-ylmethoxy)-benzoic acid methyl ester (500 mg, 1.7 mmole) in tetrahydrofuran (8.5 ml) and methanol (3 ml) was added 1N NaOH (3.4 ml, 2 eq.). The reaction mixture was stirred at ambient temperature for 16 h. To the reaction mixture was added 50 ml of brine and the pH was adjusted to 3 with 1N HCl to provide a white precipitate which was filtered and dried to provide the title compound as a white solid (463 mg, 98%). 1H NMR (400 MHz, DMSO) δ 8.39 (d, J=8.3 Hz, 1 H), 7.99 (m, 2 H), 7.81 (M, 2H), 7.76 (dt, J=8.3, 1.7 Hz, 1 H), 7.64 (d, J=8.3 Hz, 1 H), 7.60 (dt, J=7.9, 1.3 Hz, 1 H), 7.12 (M, 2 H), 5.41 (s, 2 H); MS: (M+H m/z=280.2).

후처리

  1. customto provide a white precipitate which
  2. filtrationwas filtered
  3. customdried

출처 및 근거

ORD 기록
ord-09950cb70c1747dfa8f7f9b75051c87d
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429665B2

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