Methyl iodide → Methyl 5-nitrosalicylate

HRID 71540

Reaction equation

F[C:2]1C(N)=NC(N)=NC=1.[OH:10][C:11]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].C(=O)([O-])[O-].[K+].[K+].IC>>[OH:10][C:11]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:12]=1[C:13]([O:15][CH3:2])=[O:14]

Participants

Reactant 4

HCID 6328Methyl iodide

HCID 73185-Nitrosalicylic acid

HCID 11430Potassium Carbonate

HCID 2556085-Fluoropyrimidine-2,4-diamine

Product 1

HCID 87041Methyl 5-nitrosalicylateYield 77%

Procedure

In a manner analogous to the preparation of N2,N4-bis(3-methoxy-4-methoxycarbonyl)phenyl)-5-fluoro-2,4-pyrimidinediamine, 2-hydroxy-5-nitrobenzoic acid (1 g, 5.5 mmol), potassium carbonate (3 g, 22 mmol) and iodomethane (1 mL, 16 mmol) gave methyl 2-hydroxy-5-nitrobenzoate (880 mg, 77%).

Sources & evidence

ORD record: ord-45ac2add2d5a4a28be66a6508eebb1db
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822685B2

Linked notes

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