5-Amino-2-methylphenol → 4-(3-Hydroxy-4-methyl-phenylamino)-6-methoxy-7-(3-pyridin-4-yl-propoxy)-quinoline-3-carbonitrile hydrochloride

HRID 379176Notes

Reaction equation

HRID 379176 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:24]#[N:25].[OH:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][C:33]=1[CH3:34])[NH2:30].Cl.N1C=CC=CC=1.C(OC(O)C)C>>[ClH:1].[OH:26][C:27]1[CH:28]=[C:29]([NH:30][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:24]#[N:25])[CH:31]=[CH:32][C:33]=1[CH3:34]

Participants

5

Reactant 4

HCID 178185-Amino-2-methylphenolHCID 101298981-EthoxyethanolHCID 10176127Pyridinium chlorideHCID 216973214-Chloro-6-methoxy-7-(3-pyridin-4-yl-propoxy)-quinoline-3-carbonitrile

Product 1

HCID 216973114-(3-Hydroxy-4-methyl-phenylamino)-6-methoxy-7-(3-pyridin-4-yl-propoxy)-quinoline-3-carbonitrile hydrochlorideYield 65.9%

Procedure

A mixture of 0.090 g of 4-chloro-6-methoxy-7-(3-pyridin-4-yl-propoxy)-quinoline-3-carbonitrile, 0.050 g of 3-hydroxy-4-methylaniline, 0.039 g of pyridine hydrochloride and 3 ml of ethoxyethanol was stirred under nitrogen at reflux temperature for 20 minutes. The mixture was cooled and filtered. The product was washed with saturated sodium bicarbonate, water, then dried to give 0.080 g of 4-(3-hydroxy-4-methyl-phenylamino)-6-methoxy-7-(3-pyridin-4-yl-propoxy)-quinoline-3-carbonitrile hydrochloride as a solid, dec >153° C. ; mass spectrum (electrospray, m/e): M+H 440.9.

Workup

  1. temperatureat reflux temperature for 20 minutes
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washThe product was washed with saturated sodium bicarbonate, water
  5. customdried

Sources & evidence

ORD record
ord-7ff64eff61534819a417bcf81049efc7
Source dataset
uspto-grants-2001_10
Patent number
US06297258B1

Reaction notes

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