P-Anisidine → HCID 13386234, compound

HRID 647426Notes

Reaction equation

HRID 647426 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([Cl:12])[N:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1>>[Cl:12][C:4]1[N:3]=[C:2]([NH:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

3

Reactant 2

HCID 7732P-AnisidineHCID 2986251,3-Dichloroisoquinoline

Product 1

HCID 13386234HCID 13386234, compoundYield 18.4%

Conditions

Temperature
170 °C

Procedure

A mixture of 1,3-dichloroisoquinoline (5.0 g; see Example 8) and p-anisidine (3.1 g) was heated at a temperature of 170° C. for a period of 2 hours. After cooling the product was purified by column chromatography over silica gel (eluant dichloromethane) to give 3-chloro-1-[N-(4-methoxyphenyl)amino]isoquinoline (1.32 g) mp 101° C.

Workup

  1. temperatureAfter cooling the product
  2. customwas purified by column chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-32e89c6b8c954f039638901f0a593eaf
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

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