Acetic Anhydride → HCID 13519428, compound

HRID 1980276Notes

Reaction equation

HRID 1980276 reaction equation
[C:1]([C:4]1([CH2:17][CH2:18][CH2:19][NH2:20])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:3])[NH2:2].[C:21](OC(=O)C)(=[O:23])C.C(OCC)(=O)C>C(O)=O>[C:1]([C:4]1([CH2:17][CH2:18][CH2:19][NH:20][CH:21]=[O:23])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 127612Deisopropylindecainide

Product 1

HCID 13519428HCID 13519428, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
30 °C

Procedure

To a stirred hot (50° C.) solution of 6.2 g (23 mM) of 9-carbamoyl-9-(3-aminopropyl)fluorene in 50 ml of 98% formic acid were added dropwise over ten minutes 17 ml of acetic anhydride. The reaction mixture was cooled to about 30° C. and stirred for one hour, and then added to 100 ml of ice water. The aqueous mixture was diluted by addition of 100 ml of ethyl acetate, and the organic layer was separated, washed with two 50 ml portions of 5% w/v aqueous sodium bicarbonate, twice with 5 ml portions of 1N hydrochloric acid, again with sodium bicarbonate, and finally with water. The solution was dried and the solvent was removed by evaporation under reduced pressure to provide 2.0 g of 9-carbamoyl-9-(3-formamidopropyl)fluorene. mp 160°-161° C.

Workup

  1. customthe organic layer was separated
  2. washwashed with two 50 ml portions of 5%
  3. customThe solution was dried
  4. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-f374d99fe30a4ff2bee886696a9966bf
Source dataset
uspto-grants-1985_04
Patent number
US04508735

Reaction notes

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