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

HRID 1825399Notes

Reaction equation

HRID 1825399 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 extacts 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 extacts are washed with water and brine
  5. dry with materialfinally dried (MgSO4)
  6. customEvaporation

Sources & evidence

ORD record
ord-2c297305b98e4aa8aaee32e64149403e
Source dataset
uspto-grants-2006_05
Patent number
US07045660B2

Reaction notes

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