Trimethylsilyldiazomethane → HCID 178498848, compound

HRID 350387Notes

Reaction equation

HRID 350387 reaction equation
[Cl:1][C:2]1[C:3]([OH:11])=[N:4][CH:5]=[C:6]([C:8]([OH:10])=[O:9])[CH:7]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:13]>C1C=CC=CC=1.CO>[Cl:1][C:2]1[C:3]([OH:11])=[N:4][CH:5]=[C:6]([C:8]([O:10][CH3:13])=[O:9])[CH:7]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 178524771HCID 178524771, compound

Product 1

HCID 178498848HCID 178498848, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a stirred solution of 3-chloro-2-hydroxypyridine-5-carboxylic acid (1 g, 5.762 mmol) in benzene (16 mL) and MeOH (4 mL) was added dropwise TMSCHN2 (3.17 mL, 6.338 mmol) at 0° C., and the resulting mixture was stirred overnight at room temp. The reaction mixture was quenched by the addition of AcOH and the mixture was evaporated off. The residue was suspended in water and precipitate was collected. The crude solid was washed with Et2O, and dried under a reduced pressure to give 728.1 mg (67%) methyl 3-chloro-2-hydroxypyridine-5-carboxylate as a white crystalline powder. IR (KBr) 1655, 1282, 1245, 769 cm−1; 1H-NMR (400 MHz, DMSO-d6) δ 3.79 (s, 3H), 8.01 (s, 1H), 8.06 (s, 1H); MS (FAB) m/z 188 (M++1); Anal. Calcd for C7H6ClNO3: C, 44.82; H, 3.22; Cl, 18.90; N, 7.47. Found: C, 44.74; H, 3.22; Cl, 19.00; N, 7.34.

Workup

  1. customThe reaction mixture was quenched by the addition of AcOH
  2. customthe mixture was evaporated off
  3. customprecipitate was collected
  4. washThe crude solid was washed with Et2O
  5. customdried under a reduced pressure

Sources & evidence

ORD record
ord-c748240191be46349fc13077018c62e7
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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