Acetic Anhydride → HCID 53822225, compound

HRID 1417572Notes

Reaction equation

HRID 1417572 reaction equation
CC(O[C:5]([CH3:7])=[O:6])=O.[CH3:8][C@H:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C@H:10]1[NH2:18].[OH-].[K+]>C1(C)C=CC=CC=1.O>[CH3:8][C@H:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C@H:10]1[NH:18][C:5](=[O:6])[CH3:7]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 14797Potassium HydroxideHCID 51899508HCID 51899508, compound

Product 1

HCID 53822225HCID 53822225, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of Ac2O (1.45 g, 14.2 mmole) in toluene (12 ml), was added dropwise a solution of (rac), (cis)-2-methyl-1-aminoindan (Ex. 39, 1.85 g, 12.6 mmole). The mixture was heated at 90° C. for 15 min, cooled to 70° C., and a solution of 1.1 g KOH in 8.3 ml water was added. The reaction mixture was stirred at ambient temperature for 2 hrs; the solid was collected by filtration, washed with toluene (10 ml), dried and crystallized from hexane:EtOAc, to give 1.85 g (9.8 mmole, 78%), mp: 146°-7° C.

Workup

  1. temperaturecooled to 70° C.
  2. filtrationthe solid was collected by filtration
  3. washwashed with toluene (10 ml)
  4. customdried
  5. customcrystallized from hexane
  6. customEtOAc, to give 1.85 g (9.8 mmole, 78%), mp: 146°-7° C.

Sources & evidence

ORD record
ord-a1d2291e137d43ddbb826300d669c66c
Source dataset
uspto-grants-1999_03
Patent number
US05877221

Reaction notes

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