Water → Methyl 5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine-7-carboxylate

HRID 1919684Notes

Reaction equation

HRID 1919684 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[C:5]2=[CH:12][CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:4]2[N:3]=1.[Cl:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24].O>CN1C(=O)CCC1>[Cl:20][C:21]1[CH:22]=[C:23]([NH:24][C:2]2[C:11]3[C:6](=[CH:7][N:8]=[CH:9][CH:10]=3)[C:5]3=[CH:12][CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:4]3[N:3]=2)[CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 79323-ChloroanilineHCID 50941294Methyl 5-chlorobenzo[c][2,6]naphthyridine-7-carboxylate

Product 1

HCID 57395611Methyl 5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine-7-carboxylateYield 45.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Methyl 5-chlorobenzo[c][2,6]naphthyridine-7-carboxylate (1.0 eq, 48 mg, 0.176 mmol) and 3-chloroaniline (3.0 eq, 60 ul, 0.56 mmol) were stirred under microwave heating at 120° C. in NMP (0.3 ml) for 10 minutes. Water was added and the solid isolated by filtration. Trituration in methanol and filtration afforded methyl 5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine-7-carboxylate as a solid (29 mg, 45% yield). LCMS (ES): >85% pure, m/z 364 [M+1]+.

Workup

  1. customthe solid isolated by filtration
  2. filtrationTrituration in methanol and filtration

Sources & evidence

ORD record
ord-3493b0a8708f48af938f3c89bf17924a
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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