Triphenylphosphine → 2-(4-Methoxybenzyl)-3,4-dihydro-2,6-naphthyridin-1(2H)-one

HRID 1844017ノート

反応式

HRID 1844017 の反応式
O[CH2:2][CH2:3][C:4]1[CH:21]=[N:20][CH:19]=[CH:18][C:5]=1[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=[O:7].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:8]2[CH2:2][CH2:3][C:4]3[C:5](=[CH:18][CH:19]=[N:20][CH:21]=3)[C:6]2=[O:7])=[CH:11][CH:12]=1

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 899645143-(2-hydroxyethyl)-N-(4-methoxybenzyl)isonicotinamide

生成物 1

HCID 735546032-(4-Methoxybenzyl)-3,4-dihydro-2,6-naphthyridin-1(2H)-one収率 145.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3-(2-Hydroxyethyl)-N-(4-methoxybenzyl)isonicotinamide (220 mg, 0.769 mmol) was reacted with PPh3 (403 mg, 1.538 mmol), DEAD (0.15 mL, 0.922 mmol) and THF (10 mL) to afford the crude product. Purification by column chromatography on silica gel (1% methanol in CHCl3) afforded 300 mg of the product. LCMS: 66.95%, m/z=269.0 (M+1)

後処理

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1% methanol in CHCl3)

出典と根拠

ORDレコード
ord-a1b3bcd25d6c4edebe54b0dff97e0005
出典データセット
uspto-grants-2015_02
特許番号
US08946260B2

反応ノート

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