Benzaldehyde → HCID 12972791, compound

HRID 1058619Notes

Reaction equation

HRID 1058619 reaction equation
[NH2:1][C:2]1[C:3]([CH3:28])=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:28][C:3]1[C:2]2[N:1]=[C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:12]([CH2:13][CH2:14][CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH2:17][CH2:16]3)[C:11]=2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 516892Sodium BicarbonateHCID 18668792HCID 18668792, compound

Product 1

HCID 12972791HCID 12972791, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.65 g of tert-butyl 4-[2-[(3-amino-2-methylquinolin-4-yl)amino]-ethyl]-1-piperidinecarboxylate, 0.29 g of benzaldehyde and 0.08 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in 5 ml of tetrahydrofuran was stirred at room temperature for 3 days. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried, and the solvent was evaporated to give a reddish brown liquid. The resulting liquid was purified by silica gel column chromatography using ethyl acetate—n-heptane (1:1) as an eluting solvent, and washed with diisopropyl ether to give 0.55 g of a colorless solid. Recrystallization from diisopropyl ether gave colorless crystals having the melting point of from 146 to 146.5° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. customdried
  4. customthe solvent was evaporated
  5. customto give a reddish brown liquid
  6. customThe resulting liquid was purified by silica gel column chromatography
  7. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-a893877a3ad64e418de6e2927b92dbae
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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