4-Chlorobutanal → HCID 10204932、化合物

HRID 396192

反応式

HRID 396192 の反応式
[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

参加物

8

反応物 4

HCID 2422004-ChlorobutanalHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 10177215HCID 10177215、化合物

生成物 1

HCID 10204932HCID 10204932、化合物収率 53%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6422Trifluoroacetic acid溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cab0ee58e18c45aa9816c73f9f62eff8
出典データセット
uspto-grants-2003_08
特許番号
US06608048B2

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