Hydrochloric Acid → 3-[7-[3-(dimethylamino)propyl]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid

HRID 506995노트

반응식

HRID 506995 반응식
[CH3:1][N:2]([CH3:28])[CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][N:12]([C:17]3[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=3[CH3:27])[C:20]([O:22]C)=[O:21])[C:13]2=[O:16])=[CH:8][CH:7]=1.[OH-].[Na+].Cl>CO>[CH3:28][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][N:12]([C:17]3[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=3[CH3:27])[C:20]([OH:22])=[O:21])[C:13]2=[O:16])=[CH:8][CH:7]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67018581methyl 3-[7-[3-(dimethylamino)propyl]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoate

생성물 1

HCID 670185853-[7-[3-(dimethylamino)propyl]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Methyl 3-[7-[3-(dimethylamino)propyl]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoate (176 mg) was stirred in a solution of methanol (2 ml) and 1N NaOH solution (0.57 ml) at 65° C. for 1 hour and then neutralised with 2N HCl (0.28 ml). The reaction mixture was concentrated and the residue was purified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK) using initially methanol and then a 99:1 mixture of methanol and aqueous ammonia solution to yield 3-[7-[3-(dimethylamino)propyl]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid as a cream coloured solid (155 mg); NMR Spectrum: (DMSOd6) 1.81 (m, 2H), 2.12 (s, 3H), 2.24 (s, 6H), 2.38 (t, 2H), 2.76 (t, 2H), 6.71 (d, 1H), 7.29 (d, 1H), 7.51 (d, 1H), 7.66 (m, 2H), 7.76 (s, 1H), 7.94 (d, 1H), 8.08 (s, 1H); Mass Spectrum: M+H+ 365.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK)
  3. additiona 99:1 mixture of methanol and aqueous ammonia solution

출처 및 근거

ORD 기록
ord-e5b78649e9df4df384d90d9fa78f08de
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786115B2

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