Methyl iodide → Methyl 2-amino-6-chlorobenzoate

HRID 864715

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:11])[C:7]=1[C:8]([OH:10])=[O:9].I[CH3:13].[OH-].[K+]>>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:11])[C:7]=1[C:8]([O:10][CH3:13])=[O:9]

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 14797Potassium Hydroxide

HCID 750712-Amino-6-chlorobenzoic acid

Product 1

HCID 592849Methyl 2-amino-6-chlorobenzoateYield 78.4%

Procedure

Using the procedure described above in Preparation 1, 5.0 g (0.029 mol) of 6-chloroanthranilic acid and 2.75 ml (0.044 mol) of iodomethane were reacted in the presence of 4.08 g (0.073 mol) of powdered potassium hydroxide to give 4.22 g (78%) of methyl 6-chloroanthranilate as an oil.

Sources & evidence

ORD record: ord-8cd00d734c5444f1804c2288e1aabf23
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05563163

Linked notes

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