Benzenamine, 4-chloro-2-methoxy- → HCID 67176185, compound

HRID 238405Notes

Reaction equation

HRID 238405 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([C:7]([CH:9]([CH2:15][CH:16]=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=O)=[C:5]([CH3:20])[CH:4]=1)#[N:2].[Cl:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[C:24]([O:29][CH3:30])[CH:23]=1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CCO>[Cl:21][C:22]1[CH:28]=[CH:27][C:25]([N:26]2[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:7]2[C:6]2[CH:18]=[CH:19][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[CH3:20])=[C:24]([O:29][CH3:30])[CH:23]=1

Participants

5

Reactant 3

HCID 7143Benzenamine, 4-chloro-2-methoxy-HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86654216HCID 86654216, compound

Product 1

HCID 67176185HCID 67176185, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of Intermediate C (2.5 g, 9.2 mmol) and 4-chloro-2-methoxyaniline (1.8 g, 9.2 mmol) in anhydrous EtOH (20 mL) was added PPTS (0.46 g, 0.18 mmol), and the reaction mixture was heated at 50° C. for six hours. Followed work-up procedure described in Step 1, Scheme 1 to give the desired compound, which was used in the next step without further purification.

Sources & evidence

ORD record
ord-efb053469d454ce3aab434cc09700451
Source dataset
uspto-grants-2014_02
Patent number
US08642628B2

Reaction notes

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