Sodium Nitrite → HCID 86751943, compound

HRID 726184Notes

Reaction equation

HRID 726184 reaction equation
[CH3:1][C:2]1[NH:7][C:6]2[CH2:8][O:9][C:10](=[O:11])[C:5]=2[CH:4]([C:12]2[CH:16]=[CH:15][S:14][C:13]=2[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:3]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25].N([O-])=O.[Na+]>C(O)(=O)C>[CH3:1][C:2]1[N:7]=[C:6]2[CH2:8][O:9][C:10](=[O:11])[C:5]2=[C:4]([C:12]2[CH:16]=[CH:15][S:14][C:13]=2[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:3]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 70490664HCID 70490664, compound

Product 1

HCID 86751943HCID 86751943, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.5 g of (-)-ethyl 2-methyl-4-(2-benzylthiophenyl)-5-oxo-1,4,5,7-tetrahydro-furo[3,4-b]pyridine-3-carboxylate are dissolved in 15 ml of glacial acetic acid. In the course of 10 min, 0.5 g of NaNO2 is added to the solution which is situated in an 18×180 mm test tube, nitrous gases bubbling through the solution. The batch is then immediately poured into a solution of 25 g of K2HPO4 in 50 ml of water, stirred, extracted with ethyl acetate and chromatographed on silica gel. 418 mg (84% of theory) of (+)-ethyl 2-methyl-4-(2-benzylthiophenyl)-5-oxo-5,7-dihydrofuro[3,4-b]pyridine-3-carboxylate are obtained.

Workup

  1. custombubbling through the solution
  2. additionThe batch is then immediately poured into a solution of 25 g of K2HPO4 in 50 ml of water
  3. extractionextracted with ethyl acetate
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-1ff651787caa4e708330eed284e34796
Source dataset
uspto-grants-1998_01
Patent number
US05708177

Reaction notes

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