Acetic Acid → HCID 68108076, compound

HRID 538384Notes

Reaction equation

HRID 538384 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][C:11]([C:17]#[N:18])=[CH:10][N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[C:1]([O:5][C:6]([C:8]1[C:13]([NH2:14])=[CH:12][C:11]([C:17]#[N:18])=[CH:10][N:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24489Sodium Dithionite2×HCID 68107714HCID 68107714, compound

Product 1

HCID 68108076HCID 68108076, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 5-cyano-3-nitro-pyridine-2-carboxylic acid tert-butyl ester (130 mg, 0.522 mmol) in water (3 ml) was added acetic acid (0.149 ml, 2.61 mmol), the mixture was stirred at room temperature for 20 min, sodium dithionite (454 mg, 2.61 mmol) was added and stirring was continued for 23 h. Additional sodium dithionite (182 mg, 1.043 mmol) was added and the reaction mixture stirred for another 48 h. The mixture was extracted with DCM, the combined organic layers were washed with water and saturated aq. NaCl, dried with Na2SO4 and evaporated to provide the title compound as yellow solid. The product was used for the next step without further purification.

Workup

  1. stirringstirring
  2. waitwas continued for 23 h
  3. stirringthe reaction mixture stirred for another 48 h
  4. extractionThe mixture was extracted with DCM
  5. washthe combined organic layers were washed with water and saturated aq. NaCl
  6. dry with materialdried with Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-3e8b32d435374c6e812b8bdec9b76318
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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