Isopropanol → 6-Amino-5-chloro-7-carboxy-indan-1-ol

HRID 1947776Notes

Reaction equation

HRID 1947776 reaction equation
[NH2:1][C:2]1[C:10]([C:11]#N)=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:13])=[CH:4][C:3]=1[Cl:14].[OH-:15].[Na+].C([OH:20])(C)C>>[NH2:1][C:2]1[C:10]([C:11]([OH:20])=[O:15])=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:13])=[CH:4][C:3]=1[Cl:14]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 684986706-Amino-5-chloro-7-cyanoindan-1-ol

Product 1

HCID 595494306-Amino-5-chloro-7-carboxy-indan-1-ol

Conditions

Temperature
120 °C

Procedure

A solution of the above 6-amino-5-chloro-7-cyanoindan-1-ol in isopropanol (20 ml) is treated with aqueous sodium hydroxide (380 mg in 1 ml of water) and heated at 120° C. for 15 hours. Solvent is evaporated, the residue is treated with water and washed with ethyl acetate. The aqueous layer is acidified and extracted with ethyl acetate. The separated organic layer is dried over sodium sulfate, filtered, and evaporated to give 6-amino-5-chloro-7-carboxy-indan-1-ol which is directly used in the next step. LC/MS: 228/230 (M+1)+.

Workup

  1. customSolvent is evaporated
  2. additionthe residue is treated with water
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe separated organic layer is dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e6eccf1064584c419b0e36fced65dbb7
Source dataset
uspto-grants-2013_03
Patent number
US08399490B2

Reaction notes

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