Diazomethane → Methyl 2-chloronicotinate

HRID 2058185Notes

Reaction equation

HRID 2058185 reaction equation
[N+](=[CH2:3])=[N-].N(CNC(N)=O)=O.[OH-].[K+].[Cl:13][C:14]1[N:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17]>C(OCC)C>[Cl:13][C:14]1[N:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([O:18][CH3:3])=[O:17]

Participants

6

Reactant 4

HCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 762582-Chloronicotinic acidHCID 104823Urea, (nitrosomethyl)-

Product 1

HCID 819931Methyl 2-chloronicotinate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a cold diethyl ether solution containing about 2.8 g. (0.067 mole) of diazomethane generated from 10 g. of nitrosomethyl urea and 30 cc. of 40% potassium hydroxide (see Organic Synthesis, Col. 1, Vol. II, page 166) was added in portions 9.45 g. (0.06 mole) of 2-chloronicotinic acid. After the evolution of nitrogen had ceased the reaction mixture was allowed to stand at room temperature overnight. The solvent was removed in a rotary evaporator leaving 2-chloro-nicotinic acid, methyl ester as a residual oil whose infrared spectrum indicated no OH absorption was present. The oil was used directly in the next step. The above compound has also been described by F. G. Mann and J. A. Reid, J. Chem. Soc., 1952, 2057.

Workup

  1. customThe solvent was removed in a rotary evaporator

Sources & evidence

ORD record
ord-e1063ce9d0ca46e8bdfc0af641d3b37c
Source dataset
uspto-grants-1980_07
Patent number
US04215123

Reaction notes

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