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

HRID 506995ノート

反応式

HRID 506995 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e5b78649e9df4df384d90d9fa78f08de
出典データセット
uspto-grants-2010_08
特許番号
US07786115B2

反応ノート

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