Ammonium Hydroxide → 3,5-Dichloro-3-pyridylamine

Reaction equation

Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.[OH-].[NH4+:11]>>[NH2:11][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 276662,3,5-Trichloropyridine

Product 1

HCID 778863,5-Dichloro-3-pyridylamine

Procedure

2,3,5-Trichloropyridine (20 g, 0.11 moles) was placed in a steel bomb and treated with ammonium hydroxide (300 mL) at 190° C. in similar manner as described in Example 2 to give 2-amino-3,5-dichloropyridine (15 g) as a white solid. 1H NMR (CDCl3) δ 7.92 (d, 1H), 7.48 (d, 1H), 5.1 (broad s, 2H); MS m/z 163 (M+H).

Sources & evidence

ORD record: ord-e4551d28495c451cb2bebf3e0561a601
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186714B2

Reaction notes

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