Trimethylsilyldiazomethane → HCID 178498304, compound

HRID 350390Notes

Reaction equation

HRID 350390 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>[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

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 178418479HCID 178418479, compound

Product 1

HCID 178498304HCID 178498304, compoundYield 258.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

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 mixture 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) δ 3.77 (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 mixture 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-f767ea33237d4b02a4080e4ea0b28915
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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