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Phosphorus oxybromide → 1-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid

HRID 250362
ノート
印刷プレビュー

反応式

HRID 250362 の反応式
C([O:5][C:6]([C:8]1[N:9]=[C:10](O)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])CCC.C(OC(C1N=CC2C(C=1O)=CC=C(OC1C=CC(OC)=CC=1)C=2)=O)CCC.P(Br)(Br)([Br:56])=O>C(#N)C>[Br:56][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([S:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:12]=2)[C:17]([OH:18])=[C:8]([C:6]([OH:5])=[O:7])[N:9]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24613Phosphorus oxybromideHCID 667126187-(4-Methoxy-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid butyl esterHCID 178450860HCID 178450860、化合物

生成物 1

HCID 860145681-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

1,4-Dihydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester (Example A-63 d) Compound A) (29.0 g) and phosphorous oxybromide (67.5 g) in 600 ml anhydrous acetonitrile was stirred at reflux for 4 hours. After cooling the reaction mixture was concentrated and saturated sodium bicarbonate solution and ethyl acetate were added to the residue and stirred overnight. Precipitate that formed between layers was collected and washed with water to give the title compound (10.2 g). MS-(+)-ion M+1=376.0, 378.1.

後処理

  1. temperatureat reflux for 4 hours
  2. temperatureAfter cooling the reaction mixture
  3. concentrationwas concentrated
  4. additionsaturated sodium bicarbonate solution and ethyl acetate were added to the residue
  5. customPrecipitate that formed between layers
  6. customwas collected
  7. washwashed with water

出典と根拠

ORDレコード
ord-f17dcd497741415395f7efe4173b9a5b
出典データセット
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07863292B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート