Methyl 6-chloro-5-nitronicotinate → HCID 22145708, compound

HRID 1994341Notes

Reaction equation

HRID 1994341 reaction equation
[CH3:1][S-:2].[Na+].Cl[C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][N:6]=1>CO>[CH3:1][S:2][C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 346961Methyl 6-chloro-5-nitronicotinateHCID 4378561Sodium methanethiolate

Product 1

HCID 22145708HCID 22145708, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium thiomethoxide (9.1 g) in dry methanol (50 mL) is added dropwise to a stirred solution of methyl 6-chloro-5-nitronicotinoate (25.1 g) in dry methanol (400 mL) and the mixture stirred for 4 hours. The pasty mixture is evaporated to low volume, diluted with water and the product extracted into ethyl acetate. The extracts are washed with water and brine, and finally dried (MgSO4). Evaporation gave methyl 6-methylthio-5-nitronicotinoate (16.8 g) as a yellow solid. The solid can be recrystallised from cyclohexane to give a yellow solid m.p. 115-6° C.

Workup

  1. customThe pasty mixture is evaporated to low volume
  2. additiondiluted with water
  3. extractionthe product extracted into ethyl acetate
  4. washThe extracts are washed with water and brine
  5. dry with materialfinally dried (MgSO4)
  6. customEvaporation

Sources & evidence

ORD record
ord-f1e6380b7b624213864ced6c150718fa
Source dataset
uspto-grants-2010_01
Patent number
US07652144B2

Reaction notes

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