Acetic Acid → HCID 12908984, compound

HRID 354554Notes

Reaction equation

HRID 354554 reaction equation
[F:1][C:2]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][C:6]=1[NH2:14].[C:20](OC(=O)C)(=[O:22])[CH3:21].[C:27](O)(=[O:29])[CH3:28]>O.[O-2].[O-2].[O-2].[Cr+6]>[C:20]([NH:14][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][C:5]=1[O:4][C:3]1[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:2]=1[F:1])[C:11](=[O:29])[CH2:10][CH2:9]2)(=[O:22])[CH3:21].[C:27]([NH:14][C:6]1[CH:7]=[C:8]2[C:12]([CH2:11][CH2:10][C:9]2=[O:22])=[CH:13][C:5]=1[O:4][C:3]1[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:2]=1[F:1])(=[O:29])[CH3:28]

Participants

7

Reactant 3

HCID 176Acetic Acid2×HCID 7918Acetic AnhydrideHCID 128870866-(2,4-Difluorophenoxy)-2,3-dihydro-1H-inden-5-amine

Product 2

HCID 12908984HCID 12908984, compoundHCID 12908985HCID 12908985, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent

Procedure

13.9 g of 6-(2,4-difluorophenoxy)-5-indanylamine in 93 ml of acetic acid was combined at 30° C. with 40 ml of acetic anhydride. Thereafter a solution of 11 g of chromium trioxide in 27 ml of water and 17 ml of acetic acid was added dropwise at 50° C. After another 40 minutes at 50° C., the mixture was cooled, poured on ice water, and vacuum-filtered. The residue was chromatographed over silica gel with dichloromethane-ethyl acetate, thus obtaining 9 g of 5-acetylamino-6-(2,4-difluorophenoxy)-1-indanone, mp 153° C., and subsequently 4 g of the isomeric 6-acetylamino-5-(2,4-difluorophenoxy)-1-indanone, mp 199° C.

Workup

  1. temperaturethe mixture was cooled
  2. additionpoured on ice water
  3. filtrationvacuum-filtered
  4. customThe residue was chromatographed over silica gel with dichloromethane-ethyl acetate

Sources & evidence

ORD record
ord-534865baf2334f04bf72389d58730326
Source dataset
uspto-grants-1983_03
Patent number
US04375479

Reaction notes

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