Trimethylsilyldiazomethane → HCID 178498304, compound

HRID 354310Notes

Reaction equation

HRID 354310 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:12]>C1C=CC=CC=1.CO>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:12])=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 178418479HCID 178418479, compound

Product 1

HCID 178498304HCID 178498304, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a stirred solution of 6-hydroxynicotinic acid (500 mg, 3.594 mmol) in benzene (8 mL) and MeOH (2 mL) was added dropwise TMSCHN2 (1.97 mL, 3.953 mmol) at 0° C., and the mixture was stirred overnight at room temp. The reaction mixture was quenched by the addition of AcOH, and the resulting mixture was concentrated in vacuo. The residue was chromatographed on silica-gel with n-hexane-EtOAc (1:3, v/v) as eluent to give 269.8 mg (49%) methyl 2-hydroxypyridine-5-carboxylate as a white crystalline powder. IR (KBr) 3062, 1657, 1654, 1612, 1435, 1300, 1113, 775, 642 cm−1; 1H-NMR (400 MHz, CDCl3) δ3.87 (s, 3H), 6.58 (d, J=9.8 Hz, 1H), 7.99 (dd, J=2.4, 9.8 Hz, 1H), 8.19 (d, J=2.4 Hz, 1H); MS (FAB) m/z 154 (M++1); Anal. Calcd. for C7H7NO3.1/4H2O: C, 53.33; H, 4.80; N, 8.89. Found: C, 53.58; H, 4.65; N, 8.87.

Workup

  1. customThe reaction mixture was quenched by the addition of AcOH
  2. concentrationthe resulting mixture was concentrated in vacuo
  3. customThe residue was chromatographed on silica-gel with n-hexane-EtOAc (1:3

Sources & evidence

ORD record
ord-c7c2ded724544035a7de147a77b977dc
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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