Trimethylsilyldiazomethane → HCID 178498304, compound

HRID 354328Notes

Reaction equation

HRID 354328 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 258.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a stirred solution of 6-hydroxynicotinic acid (2 g, 14.38 mmol) in benzene (32 mL) and MeOH (8 mL) was added dropwise TMSCHN2 (1.97 mL, 3.953 mmol) at 0° C., and the resulting mixture was stirred for 2 hr at room temp. The mix was quenched by the addition of AcOH and concentrated in vacuo. The residue was suspended in water and the solid was collected. The crude solid was washed with Et2O, and dried in vacuo to give 1.566 g (71%) methyl 2-hydroxypyridine-5-carboxylate as a pale brown crystalline powder. IR (KBr) 1655, 1645, 1610, 1433, 1300, 1113, 777, 642 cm−1; 1H-NMR (400 MHz, DMSO-d6) δ3.77 (s, 3H), 6.37 (d, J=9.8 Hz, 1H), 7.99 (dd, J=2.4, 9.8 Hz, 1H), 8.03 (d, J=2.4 Hz, 1H); MS (FAB) m/z 154 (M++1); Anal. Calcd. for C7H7NO3: C, 54.90; H, 4.61; N, 9.15. Found: C, 54.89; H, 4.60; N, 9.13.

Workup

  1. customThe mix was quenched by the addition of AcOH
  2. concentrationconcentrated in vacuo
  3. customthe solid was collected
  4. washThe crude solid was washed with Et2O
  5. customdried in vacuo

Sources & evidence

ORD record
ord-3ad7948ac5ad492ba02727469def0e9a
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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