Trifluoroacetic acid → HCID 15231616, compound

HRID 258042Notes

Reaction equation

HRID 258042 reaction equation
C(OC([NH:8][C:9]1[C:10](=[O:29])[O:11][C:12]2[CH:25]=[C:24]3[CH2:26][CH2:27][CH2:28][C:23]3=[CH:22][C:13]=2[C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][C:9]1[C:10](=[O:29])[O:11][C:12]2[CH:25]=[C:24]3[CH2:26][CH2:27][CH2:28][C:23]3=[CH:22][C:13]=2[C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 197821663-tert-butyloxycarbonylamino-4-(2-methylphenyl)-7,8-dihydro-6H-cyclopenta[g][1]benzopyran-2-one

Product 1

HCID 15231616HCID 15231616, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-tert-butyloxycarbonylamino-4-(2-methylphenyl)-7,8-dihydro-6H-cyclopenta[g][1]benzopyran-2-one (2.05 g) in dichloromethane (20 ml) was added trifluoroacetic acid (10 ml) dropwise with ice-cooling. The mixture was stirred under ice-cooling for 1 hour, after which the solvent was distilled off. The residue was diluted with water, neutralized with saturated aqueous solution of NaHCO3 and extracted with chloroform. The extract was washed with water and dried (MgSO4) and the solvent was distilled off to give crystals of 3-amino-4-(2-methylphenyl)-7,8-dihydro-6H-cyclopenta[g][1]-benzopyran-2-one (1.5 g, 98.4%). Recrystallization from ethanol-dichloromethane gave colorless prisms, m.p. 275°-276° C.

Workup

  1. temperaturecooling
  2. temperaturecooling for 1 hour
  3. distillationafter which the solvent was distilled off
  4. additionThe residue was diluted with water
  5. extractionextracted with chloroform
  6. washThe extract was washed with water
  7. dry with materialdried (MgSO4)
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-d93613a7591841e4aa6868f13bb9c091
Source dataset
uspto-grants-1993_11
Patent number
US05264454

Reaction notes

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