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

HRID 548479Notes

Reaction equation

HRID 548479 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-ff9dd915a63744648e4526a5f1bedcc7
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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