Sodium Dithionite → HCID 178509329, compound

HRID 707467Notes

Reaction equation

HRID 707467 reaction equation
[N+:1]([C:4]1[S:8][C:7]([CH:9]=[O:10])=[CH:6][C:5]=1[C:11]1[NH:15][N:14]=[CH:13][CH:12]=1)([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)C.O>[NH2:1][C:4]1[S:8][C:7]([CH:9]=[O:10])=[CH:6][C:5]=1[C:11]1[CH:12]=[CH:13][NH:14][N:15]=1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 86705379HCID 86705379, compound

Product 1

HCID 178509329HCID 178509329, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

5-Nitro-4-(1H-pyrazol-5-yl)thiophene-2-carbaldehyde (40 mg, 0.18 mmol) was dissolved in absolute ethanol (4 mL). A saturated solution of sodium hydrosulfite in water was added dropwise until complete consumption of the starting material (10 minutes). Water (30 mL) added, the aqueous layer extracted with ethyl acetate (3×10 mL), and the resulting organics were dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography, eluting with ethyl acetate in hexanes, to yield 5-amino-4-(1H-pyrazol-3-yl)thiophene-2-carbaldehyde as a powder (11 mg, 42%). 1H NMR (400 MHZ, DMSO-d6) δ 6.60 (d, J 2.3 Hz, 1H), 7.80 (d, J 2.3 Hz, 1H), 8.02 (s, 1H), 9.49 (s, 1H).

Workup

  1. extractionthe aqueous layer extracted with ethyl acetate (3×10 mL)
  2. dry with materialthe resulting organics were dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by flash chromatography
  5. washeluting with ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7ad56cfb04c146d7b4ff7f5f0a8ba64b
Source dataset
uspto-grants-2015_11
Patent number
US09175010B2

Reaction notes

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