Sodium Carbonate → 4-(3-Hydroxy-4-methyl-phenylamino)-6-methoxy-quinoline-3-carbonitrile

HRID 612191Notes

Reaction equation

HRID 612191 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:15].[NH2:16][C:17]1[CH:22]=[C:21]([OH:23])[C:20]([CH3:24])=[CH:19][CH:18]=1.Cl.N1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCCO)C.O>[OH:23][C:21]1[CH:22]=[C:17]([NH:16][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:14]#[N:15])[CH:18]=[CH:19][C:20]=1[CH3:24]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 178185-Amino-2-methylphenolHCID 10176127Pyridinium chlorideHCID 224667634-Chloro-6-methoxy-quinoline-3-carbonitrile

Product 1

HCID 224666274-(3-Hydroxy-4-methyl-phenylamino)-6-methoxy-quinoline-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8076Glycol monoethyl etherSolvent

Procedure

To a suspension of 218.6 mg (1.0 mmol) of 4-chloro-6-methoxy-3-quinolinecarbonitrile and 147.8 mg (1.20 mmol) of 5-amino-o-cresol in 10 mL of 2-ethoxyethanol was added 115.6 mg (1.0 mmol) of pyridine hydrochloride. The resulting reaction mixture was refluxed for 1 hr, and then the solvent was removed to give a residue. To the residue was added about 30 mL of water and neutralized to pH 7-8 by addition of diluted sodium carbonate solution. The precipitate was collected by filtration and washed with water and ether. After drying in vacuo, this afforded 278.3 mg (91%) of the product as a yellow solid, m.p.>250° C. (dec.), mass (electrospray, m/e): M+H 305.9.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 1 hr
  3. customthe solvent was removed
  4. customto give a residue
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water and ether
  7. customAfter drying in vacuo

Sources & evidence

ORD record
ord-e3188d1422604309a4ef26f2b3ee55e8
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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