Nitric Acid → 7-nitro-2,3-dihydro-2-trifluoroacetyl-1H-Benz[de]isoquinoline-6-sulfonyl chloride

HRID 1068561Notes

Reaction equation

HRID 1068561 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([N:5]1[CH2:14][C:13]2[CH:15]=[CH:16][C:17]([S:18]([Cl:21])(=[O:20])=[O:19])=[C:11]3[C:12]=2[C:7](=[CH:8][CH:9]=[CH:10]3)[CH2:6]1)=[O:4].[N+:24]([O-])([OH:26])=[O:25]>>[N+:24]([C:10]1[C:11]2[C:12]3[C:7](=[CH:8][CH:9]=1)[CH2:6][N:5]([C:3](=[O:4])[C:2]([F:1])([F:22])[F:23])[CH2:14][C:13]=3[CH:15]=[CH:16][C:17]=2[S:18]([Cl:21])(=[O:19])=[O:20])([O-:26])=[O:25]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 211896072,3-dihydro-2-trifluoroacetyl-1H-Benz[de]isoquinoline-6-sulfonyl chloride

Product 1

HCID 211896017-nitro-2,3-dihydro-2-trifluoroacetyl-1H-Benz[de]isoquinoline-6-sulfonyl chloride

Conditions

Temperature
0 °C

Procedure

Solid 2,3-dihydro-2-trifluoroacetyl-1H-Benz[de]isoquinoline-6-sulfonyl chloride (6 mmol) is added portionwise to cold (0° C.) 90% nitric acid (5 mL). The resulting mixture is stirred at 0° C. overnight then cautiously poured into ice-water. The precipitate is collected by filtration and washed with ice-water to give the title compound. The crude product can be purified by recrystallization or chromatography.

Workup

  1. filtrationThe precipitate is collected by filtration
  2. washwashed with ice-water

Sources & evidence

ORD record
ord-779bc253db9842ff9d92ac1da5e02ec6
Source dataset
uspto-grants-2001_06
Patent number
US06251890B1

Reaction notes

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