Sodium Methoxide → HCID 136351944, compound

HRID 1268889Notes

Reaction equation

HRID 1268889 reaction equation
C[O-].[Na+].C([O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][C:9]=1/[CH:16]=[CH:17]/[C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][N:19]=1)(=O)C>CO>[OH:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][C:9]=1/[CH:16]=[CH:17]/[C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][N:19]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86596992HCID 86596992, compound

Product 1

HCID 136351944HCID 136351944, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Sodium methoxide (2.29 g, 42.4 mmol) was added to a suspension of 6-[E-2-(-2-acetoxy-5-methylsulfanylphenyl)-vinyl]-nicotinic acid, methyl ester (13.26 g, 38.55 mmol) in methanol (200 mL). The mixture was heated at 60° C. for 3 hours. The reaction mixture was concentrated in vacuo and water was added followed by enough hydrochloric acid (1 M) to acidify the solution. The resultant precipitate was isolated by filtration, washed with water and dried in vacuo. This procedure afforded the product as a yellow solid (8.8 g, 76%) m/z (LCMS) (ESI+) 302 (MH+); (ESI−) 300 (M—H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and water
  2. additionwas added

Sources & evidence

ORD record
ord-f235bcb6fd5f429cb2f23e96c89ba18d
Source dataset
uspto-grants-2007_04
Patent number
US07199140B2

Reaction notes

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