4-Chlorobutanal → HCID 10204932, compound

HRID 396192

Reaction equation

HRID 396192 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:3]=1[NH:4][C:5]1[C:14]2[CH:13]=[C:12]3[O:15][CH2:16][CH2:17][NH:18][C:11]3=[CH:10][C:9]=2[N:8]=[CH:7][C:6]=1[C:19]#[N:20].[Cl:26][CH2:27][CH2:28][CH2:29][CH:30]=O.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O.O1CCCC1.FC(F)(F)C(O)=O>[Cl:26][CH2:27][CH2:28][CH2:29][CH2:30][N:18]1[C:11]2[C:12](=[CH:13][C:14]3[C:5]([NH:4][C:3]4[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:2]=4[Cl:1])=[C:6]([C:19]#[N:20])[CH:7]=[N:8][C:9]=3[CH:10]=2)[O:15][CH2:16][CH2:17]1

Participants

8

Reactant 4

HCID 2422004-ChlorobutanalHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 10177215HCID 10177215, compound

Product 1

HCID 10204932HCID 10204932, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolvent

Procedure

An amount of 100 mg (0.27 mmol) of 9-(2,4-dichloroanilino)-3,4-dihydro-2H-[1,4]oxazino[2,3-g]quinoline-8-carbonitrile, was stirred in N,N-dimethylformamide (2 mL), and to this was added a solution of 4-chloro-butyraldehyde (719 mg, 6.8 mmol) in tetrahydrofuran (2 mL) and trifluoroacetic acid (1.4 mL). The reaction mixture was stirred at room temperature, and to this was added sodium borohydride (128 mg, 3.4 mmol) portionwise, in 1.5 hours. The mixture was stirred for 16 hours, basified with saturated sodium bicarbonate solution, and extracted with ethyl acetate. After separation of the layers, the organic layer was washed with saturated brine solution, dried over sodium sulfate and evaporated to an oil. Purification was done by flash chromatography (10% acetone in dichloromethane) to give a yellow solid (66 mg, 53% yield), m.p 56-57° C.; 1H NMR (DMSO-d6) δ 9.92 (bs, 1H), 8.59 (s, 1H), 7.81 (d, 2H), 7.51 (m, 2H), 6.98 (s, 1H), 4.30 (t, 2H), 3.70 (t, 2H), 3.57 (t, 2H), 3.51 (t, 2H), 1.80 (m, 4H); HRMS (EI) m/z 461.06917 (M+1). Analysis for C22H19Cl3N4O.0.7CH3CO2C2H5.3.9H2O Found: C, 49.81; H, 3.78; N, 9.65. Calcd: C, 50.12; H, 5.46; N, 9.43.

Workup

  1. stirringThe mixture was stirred for 16 hours
  2. extractionextracted with ethyl acetate
  3. customAfter separation of the layers
  4. washthe organic layer was washed with saturated brine solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated to an oil
  7. customPurification

Sources & evidence

ORD record
ord-cab0ee58e18c45aa9816c73f9f62eff8
Source dataset
uspto-grants-2003_08
Patent number
US06608048B2

Linked notes

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