Sodium Hydroxide → 3-Amino-2-chloro-4-methylpyridine

Reaction equation

[Cl:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[C:10]1C(C(N)=O)=C(C)C=CN=1.[OH-].[Na+].BrBr>>[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([CH3:10])[CH:5]=[CH:4][N:3]=1

Participants

Reactant 4

HCID 14798Sodium Hydroxide

HCID 24408Bromine

HCID 805282-Chloro-3-pyridylamine

HCID 109428862-Chloro-4-methylpyridine-3-carboxamide

Product 1

HCID 27563873-Amino-2-chloro-4-methylpyridineYield 90%

Procedure

In a manner similar to that described for 2-chloro-3-aminopyridine in Example 14, the title compound was prepared in 90% yield (m.p. 63°-66° C., uncorrected) from 2.57 g of 2-chloro-4-methyl-3-pyridinecarboxamide, 2.28 g of NaOH, and 3.1 g of bromine.

Sources & evidence

ORD record: ord-dc49db542cfc4b73ad2b4ed7f83843e0
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05493028

Reaction notes

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