Chlorosuccinimide → 6-Amino-5-chloro-7-cyanoindan-1-ol

HRID 1947775ノート

反応式

HRID 1947775 の反応式
[NH2:1][C:2]1[C:10]([C:11]#[N:12])=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:13])=[CH:4][CH:3]=1.[Cl:14]N1C(=O)CCC1=O.[BH4-].[Na+]>O1CCCC1>[NH2:1][C:2]1[C:10]([C:11]#[N:12])=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:13])=[CH:4][C:3]=1[Cl:14]

参加物

5

反応物 3

HCID 31398ChlorosuccinimideHCID 4311764Sodium borohydrideHCID 59549438HCID 59549438、化合物

生成物 1

HCID 684986706-Amino-5-chloro-7-cyanoindan-1-ol収率 47.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 6-amino-7-cyanoindan-1-ol (700 mg, 4 mmol) in tetrahydrofuran (50 ml) is treated with N-chlorosuccinimide (530 mg, 4 mmol) in portions over 20 minutes, stirred for 30 minutes, treated with sodiumborohydride (270 mg), and stirred for one hour. The mixture is quenched with water (30 ml), evaporated to remove tetrahydrofuran, and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered, and evaporated to give 6-amino-5-chloro-7-cyanoindan-1-ol (400 mg) which is directly used in the next step; LC/MS: 209/211 (M+1)+.

後処理

  1. stirringstirred for one hour
  2. customThe mixture is quenched with water (30 ml)
  3. customevaporated
  4. customto remove tetrahydrofuran
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-67bd9fa8040e49df99a26dd4a0e4422a
出典データセット
uspto-grants-2013_03
特許番号
US08399490B2

反応ノート

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