Potassium Carbonate → 4-(3-Bromophenylmethylamino)-6,7-diethoxy-3-quinolinecarbonitrile

HRID 612023

Reaction equation

HRID 612023 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].[Br:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][NH2:25].C(N(C(C)C)CC)(C)C.C(OC(O)C)C.C(=O)([O-])[O-].[K+].[K+]>O.CCCCCC>[Br:20][C:21]1[CH:22]=[C:23]([CH2:24][NH:25][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:18]#[N:19])[CH:26]=[CH:27][CH:28]=1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 457587Benzenemethanamine, 3-bromo-HCID 101298981-EthoxyethanolHCID 107788724-Chloro-6,7-diethoxyquinoline-3-carbonitrile

Product 1

HCID 224666864-(3-Bromophenylmethylamino)-6,7-diethoxy-3-quinolinecarbonitrileYield 68.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

A stirred mixture of 4-chloro-6,7-diethoxy-3-quinolinecarbonitrile (0.69 g, 2.5 mmol), 3-bromobenzylamine (0.78 g, 3.5 mmol), diisopropylethyl amine (1.05 ml, 6.0 mmol), and 7.5 ml of ethoxyethanol was refluxed for 4 h, cooled, and stirred with a mixture of hexane and water containing 0.4 g of potassium carbonate for 3 h. The resulting solid was filtered, washed with water, and dried. Recrystallization from acetone-hexane gave 0.73 g of off-white solid, mp 156-159° C.

Workup

  1. temperaturewas refluxed for 4 h
  2. temperaturecooled
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. customdried
  6. customRecrystallization from acetone-hexane

Sources & evidence

ORD record
ord-13c5435b19b741f89787b2b48a2cc35d
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Linked notes

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