Acetic Acid → HCID 66803632, compound

HRID 1844050Notes

Reaction equation

HRID 1844050 reaction equation
C(O)(=O)C.[F:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[N+:16]([O-])=O)[C:12](=[O:19])[N:11]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][C:25]=1[C:26]([F:29])([F:28])[F:27])[CH2:10][CH2:9]2.C(OCC)(=O)C>C1COCC1.CCCCCC.[Fe]>[NH2:16][C:15]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][N:11]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][C:25]=3[C:26]([F:28])([F:29])[F:27])[C:12]2=[O:19])=[CH:7][C:6]=1[F:5]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 66803774HCID 66803774, compound

Product 1

HCID 66803632HCID 66803632, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
70 °C

Procedure

Iron powder (431.4 mg, 7.72) and acetic acid (10 mL) were added to a stirred solution of 6-fluoro-7-nitro-2-(4-(trifluoromethyl)pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one (I-79a: 550 mg, 1.54 mmol) in THF (5 mL). The resulting mixture was stirred for 4 hours at 70° C. The reaction was monitored by TLC (30% ethyl acetate in hexane). The catalyst was filtered through celite bed and the solvent concentrated under reduced pressure to afford 400 mg of the product (80% yield).

Workup

  1. filtrationThe catalyst was filtered through celite bed
  2. concentrationthe solvent concentrated under reduced pressure

Sources & evidence

ORD record
ord-a13be6d0cbba4490a4cd380a0b4304c5
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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