Ammonia → HCID 20080676, compound

HRID 1653756Notes

Reaction equation

[I:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)=[C:6]([CH:11]=1)[C:7](OC)=[O:8].C(Cl)(=O)C(Cl)=O.[NH3:30]>>[I:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)=[C:6]([CH:11]=1)[C:7]([NH2:30])=[O:8]

Participants

Reactant 3

HCID 222Ammonia

HCID 65578Oxalyl chloride

HCID 20080626HCID 20080626, compound

Product 1

HCID 20080676HCID 20080676, compound

Procedure

Using the procedure described in Example 5, 2-bromomethylnaphthalene was reacted with methyl 5-iodosalicylate to give methyl 5-iodo-2-(naphth-2-ylmethoxy)benzoate (68%). Using conventional procedures the ester was hydrolysed with base to give the corresponding acid; the acid chloride was prepared by reaction with oxalyl chloride; and the acid chloride was reacted with ethanolic ammonia to give 5-iodo-2-(naphth-2-ylmethoxy)benzamide (84% from the ester), m.p. 163° C. The benzamide so obtained was reacted with trifluoroacetic anhydride in the presence of pyridine and dimethoxyethane as reaction solvent. There was thus obtained 3-cyano-4-(naphth-2-ylmethoxy)phenyl iodide (72%), m.p. 108°-110° C.

Workup

customto give the corresponding acid

Sources & evidence

ORD record: ord-db1b3eca360a4f978c2ef5cbd5dee2d1
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05403859

Reaction notes

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