Sodium Nitrite → N-(6-chloro-8-nitro-9H-beta-carbolin-4-yl)-2,2,2-trifluoro-acetamide

HRID 552213Notes

Reaction equation

HRID 552213 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[C:6]([NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[C:5]2=1.[N:22]([O-:24])=[O:23].[Na+]>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:22]([O-:24])=[O:23])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[C:6]([NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[C:5]2=1

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 86007194N-(6-chloro-9H-beta-carbolin-4-yl)-2,2,2-trifluoro-acetamide

Product 1

HCID 86595094N-(6-chloro-8-nitro-9H-beta-carbolin-4-yl)-2,2,2-trifluoro-acetamideYield 92%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N-(6-chloro-9H-β-carbolin-4-yl)-2,2,2-trifluoro-acetamide (125 mg, 0.4 mmol, 1 equiv.) was dissolved in 2 ml TFA and NaNO2 (541 mg, 7.84 mmol, 2 equiv.) was added in one portion. The solution was stirred at room temperature for 4 hr. Volatiles were removed by rotovap, and the resulting oily orange solids were suspended in water, neutralized with a saturated aqueous sodium bicarbonate solution and filtered to give 132 mg (92%) of N-(6-chloro-8-nitro-9H-β-carbolin-4-yl)-2,2,2-trifluoro-acetamide. 1H-NMR (300 MHz, DMSO-d6): δ 12.87 (s, 1H), 12.03 (s, 1H), 9.11 (s, 1H), 8.56 (s, 1H), 8.53 (s, 1H), 8.26 (s, 1H). Formic acid standard conditions. DAD RT=2.27 min. M+H=359.

Workup

  1. customVolatiles were removed by rotovap
  2. filtrationfiltered

Sources & evidence

ORD record
ord-5dbbd69901574b1887a712daa24ed07d
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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