Dimethylamine → HCID 14780583, compound

HRID 1650137Notes

Reaction equation

HRID 1650137 reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:21][NH:22][CH3:23]>C1(C)C=CC=CC=1>[CH3:21][N:22]([CH3:23])[C:2]1[C:11]([CH:12]=[O:13])=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 14780582HCID 14780582, compound

Product 1

HCID 14780583HCID 14780583, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Chloro-4-(4-fluorophenyl)-3-quinolinecarboxaldehyde (5.28 g) and 15 ml of dimethylamine are dissolved in 75 ml of toluene. This mixture is autoclaved for 14 hours at 123°-136° C. The mixture is cooled, evaporated to dryness, and partitioned between ethyl acetate and a saturated aqueous solution of potassium carbonate. The ethyl acetate layer is dried (magnesium sulfate) and evaporated to give an orange oil. Chromatography (silica, 10% ethyl acetate/hexanes) gives 4.20 g of 2-(dimethylamino)-4-(4-fluorophenyl)-3-quinolinecarboxaldehyde as an orange solid; 1H NMR (chloroform-d): δ 9.73 (s, 1H), 7.78-6.96 (m, 8H), 3.10 (s, 6H) ppm.

Workup

  1. temperatureThe mixture is cooled
  2. customevaporated to dryness
  3. custompartitioned between ethyl acetate
  4. dry with materialThe ethyl acetate layer is dried (magnesium sulfate)
  5. customevaporated
  6. customto give an orange oil

Sources & evidence

ORD record
ord-e7cc5a8b804b4940bffb681fe31d6b24
Source dataset
uspto-grants-1990_05
Patent number
US04923861

Reaction notes

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