3-Methoxyaniline → 6-Iodo-4-(3-methoxyphenylamino)quinoline-3-carbonitrile

HRID 1935183Notes

Reaction equation

HRID 1935183 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]#[N:14].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20]>>[I:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:13]#[N:14])=[C:2]2[NH:20][C:19]1[CH:21]=[CH:22][CH:23]=[C:17]([O:16][CH3:15])[CH:18]=1

Participants

3

Reactant 2

HCID 108243-MethoxyanilineHCID 224667694-Chloro-6-iodoquinoline-3-carbonitrile

Product 1

HCID 224667756-Iodo-4-(3-methoxyphenylamino)quinoline-3-carbonitrile

Procedure

Prepared from 1.00 g of 4-chloro-6-iodoquinoline-3-carbonitrile and 0.469 g of 3-methoxyaniline in the same manner as EXAMPLE 377. The crude product was filtered through silica gel with 20% EtOAc in CH2Cl2, evaporated and dried in vacuo (50° C.). The yield of 6-iodo-4-(3-methoxyphenylamino)quinoline-3-carbonitrile was 1.09 g as yellow crystals: mass spectrum (electrospray, m/e): M+H 401.9.

Workup

  1. filtrationThe crude product was filtered through silica gel with 20% EtOAc in CH2Cl2
  2. customevaporated
  3. customdried in vacuo (50° C.)

Sources & evidence

ORD record
ord-7c42541f9d57427c88a5e954178e4c7e
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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