Sodium Iodide → Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

HRID 2205405ノート

反応式

HRID 2205405 の反応式
CO[C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:5]=1[CH2:17]Cl.[CH3:20][O:21][C:22](=[O:35])[CH2:23][NH:24]S(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].C[O-].[Na+]>CN(C=O)C.CO.O.C(O)(=O)C>[CH3:20][O:21][C:22]([C:23]1[N:24]=[CH:17][C:5]2[C:4]([C:3]=1[OH:19])=[CH:9][CH:8]=[C:7]([O:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH:6]=2)=[O:35]

参加物

10

反応物 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 562880Methyl 2-(4-methylphenylsulfonamido)acetateHCID 10942334Sodium MethoxideHCID 86709143Methyl 2-(chloromethyl)-4-phenoxybenzoate

生成物 1

HCID 86709142Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A reactor was charged with a solution of 2-chloromethyl-4-phenoxybenzoic acid methyl ester (˜68 Kg) in DMF, and stirring was initiated. The reactor was then charged with p-toluenesulfonylglycine methyl ester (66 Kg), potassium carbonate (60 Kg), and sodium iodide (4 Kg). The mixture was heated to at least 50° C. until reaction completion. The mixture was cooled. Sodium methoxide in methanol was charged and the mixture was stirred until reaction completion. Acetic acid and water were added, and the mixture was stirred, filtered and washed with water. Solid was purified by acetone trituration and dried in an oven giving 1a (Yield from step b): 58%; HPLC: 99.4%). 1H NMR (200 MHz, DMSO-d6) δ 11.60 (s, 1 H), 8.74 (s, 1H), 8.32 (d, J=9.0 Hz, 1 H), 7.60 (dd, J=2.3 & 9.0 Hz, 1H), 7.49 (m, 3 H), 7.24 (m, 3 H), 3.96 (s, 3 H); MS-(+)-ion M+1=296.09

後処理

  1. temperatureThe mixture was heated to at least 50° C. until reaction completion
  2. temperatureThe mixture was cooled
  3. stirringthe mixture was stirred until reaction completion
  4. stirringthe mixture was stirred
  5. filtrationfiltered
  6. washwashed with water
  7. customSolid was purified by acetone trituration
  8. customdried in an oven

出典と根拠

ORDレコード
ord-8b3f89d16d7e4e5b94cb068c972aceac
出典データセット
uspto-grants-2016_06
特許番号
US09371288B2

反応ノート

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