4-Chloro-2-fluoroaniline → HCID 22646544, compound

HRID 393640Notes

Reaction equation

HRID 393640 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][CH:4]=1.[Cl:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[C:27]([F:32])[CH:26]=1>CC(O)CCC>[ClH:2].[Cl:24][C:25]1[CH:31]=[CH:30][C:28]([NH:29][C:3]2[C:12]3[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][CH2:18][N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[C:10]([O:13][CH3:14])[CH:11]=3)[N:6]=[CH:5][CH:4]=2)=[C:27]([F:32])[CH:26]=1

Participants

4

Reactant 2

HCID 938984-Chloro-2-fluoroanilineHCID 22646629HCID 22646629, compound

Product 1

HCID 22646544HCID 22646544, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 223862-PentanolSolvent

Procedure

Using an analogous procedure to that described for Example 15, 4-chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinoline hydrochloride (236 mg, 0.6 mmol), (prepared as described for the starting material in Example 31), was reacted with 4-chloro-2-fluoroaniline (80 μl, 0.72 mmol) in 2-pentanol (5 ml) to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinoline hydrochloride (124 mg, 42%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-112b7763e08f4469aca4beb4f37cbc1d
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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