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Sodium Carbonate → 4-(3-Hydroxy-4-methyl-phenylamino)-6,7,8-trimethoxy-quinoline-3-carbonitrile

HRID 612149
Notes
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Reaction equation

HRID 612149 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:16][CH3:17])[C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].[NH2:20][C:21]1[CH:26]=[C:25]([OH:27])[C:24]([CH3:28])=[CH:23][CH:22]=1.C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[OH:27][C:25]1[CH:26]=[C:21]([NH:20][C:2]2[C:11]3[C:6](=[C:7]([O:16][CH3:17])[C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:18]#[N:19])[CH:22]=[CH:23][C:24]=1[CH3:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 178185-Amino-2-methylphenolHCID 101298981-EthoxyethanolHCID 224666114-Chloro-6,7,8-trimethoxy-3-quinolinecarbonitrile

Product 1

HCID 224666104-(3-Hydroxy-4-methyl-phenylamino)-6,7,8-trimethoxy-quinoline-3-carbonitrileYield 76.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.279 g of 4-chloro-6,7,8-trimethoxy-quinoline-3-carbonitrile, 0.148 g of 5-amino-o-cresol, and 10 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 30 minutes. The mixture was cooled and added to 100 ml of water. To this mixture was added sodium carbonate to pH 9. The product was collected, washed with water, and dried to give 0.279 g of 4-(3-hydroxy-4-methyl-phenylamino)-6,7,8-trimethoxy-quinoline-3-carbonitrile as a solid, mp 200° C. (decomposed); mass spectrum (EI, m/e): M 365.1356.

Workup

  1. temperatureat reflux temperature for 30 minutes
  2. temperatureThe mixture was cooled
  3. customThe product was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-9e5ea2e9d6254ff98902ca7e0bd196f8
Source dataset
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06002008

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes