Nitric Acid → 3-Bromo-2-methyl-7-nitrothieno[3,2-c]pyridin-4(5h)-one

HRID 2390622Notes

Reaction equation

HRID 2390622 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[C:10]2[C:11](=[O:15])[NH:12][CH:13]=[CH:14][C:9]=2[S:8][C:7]=1[CH3:16]>S(=O)(=O)(O)O.C1N(COCCO)C2NC(N)=NC(=O)C=2N=1>[Br:5][C:6]1[C:10]2[C:11](=[O:15])[NH:12][CH:13]=[C:14]([N+:1]([O-:4])=[O:2])[C:9]=2[S:8][C:7]=1[CH3:16]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 184507693-Bromo-2-methylthieno[3,2-c]pyridin-4(5H)-one

Product 1

HCID 184507673-Bromo-2-methyl-7-nitrothieno[3,2-c]pyridin-4(5h)-oneYield 64%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 178508935HCID 178508935, compoundSolvent

Conditions

Temperature
0 °C

Procedure

A solution of nitric acid (1.68 mL, 70%, 26.8 mmol) in sulfuric acid (5 mL) was added dropwise to a 0° C. solution of Example 66A (3.27 g, 13.4 mmol) in sulfuric acic (15 mL). The resulting mixture was stirred at 0° C. for 1 hour, warmed to room temperature overnight, and poured into ice water. The resulting precipitate was collected by filtration, washed with water, and dried in a vacuum oven to provide 2.47 g (64% yield) of the desired product. MS (ESI(+)) m/e 290 (M+H)+.

Workup

  1. temperaturewarmed to room temperature overnight
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-a85d026dc20646d69896e0c704f821c0
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

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