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

HRID 1947775Notes

Reaction equation

HRID 1947775 reaction equation
[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]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 4311764Sodium borohydrideHCID 59549438HCID 59549438, compound

Product 1

HCID 684986706-Amino-5-chloro-7-cyanoindan-1-olYield 47.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-67bd9fa8040e49df99a26dd4a0e4422a
Source dataset
uspto-grants-2013_03
Patent number
US08399490B2

Reaction notes

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