2-(Chloromethyl)anisole → HCID 10907363, compound

HRID 1940579Notes

Reaction equation

HRID 1940579 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Cl.[O:11]1[C:16]2[CH:17]=[CH:18][C:19]([C:21]3[C:22]4[O:35][C:34]5[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=5[C:23]=4[NH:24][C:25](=[O:32])[C:26]=3[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:20][C:15]=2[O:14][CH2:13][CH2:12]1>ClCCl.CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+]>[O:11]1[C:16]2[CH:17]=[CH:18][C:19]([C:21]3[C:22]4[O:35][C:34]5[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=5[C:23]=4[N:24]([CH2:5][C:4]4[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=4[O:2][CH3:1])[C:25](=[O:32])[C:26]=3[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:20][C:15]=2[O:14][CH2:13][CH2:12]1.[O:11]1[C:16]2[CH:17]=[CH:18][C:19]([C:21]3[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:25]([O:32][CH2:5][C:4]4[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=4[O:2][CH3:1])[N:24]=[C:23]4[C:33]5[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=5[O:35][C:22]=34)=[CH:20][C:15]=2[O:14][CH2:13][CH2:12]1

Participants

7

Reactant 2

HCID 814952-(Chloromethyl)anisoleHCID 11111946HCID 11111946, compound

Product 2

HCID 10907363HCID 10907363, compoundHCID 11733961HCID 11733961, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 10796Cesium carbonateSolvent

Procedure

A 50% solution of 1.8 g of 2-methoxybenzyl chloride ("A") in dichloromethane is added to a solution of 2.0 g of ethyl 4-(1,4-benzodioxan-6-yl)-1,2-dihydro-2-oxobenzofuro[3,2-b]pyridine-3-carboxylate (obtainable by reaction of 3-amino-2-(1,4-benzodioxan-6-carbonyl)benzofuran and diethyl malonate in acetone and potassium carbonate, m.p. 255°; 3-amino-2-(1,4-benzodioxan-6-carbonyl)benzofuran is obtainable by reaction of 2-hydroxybenzonitrile and 6-bromoacetyl-1,4-benzodioxane, m.p. 157°) in 15 ml of DMF and 2.5 g of caesium carbonate. The reaction mixture is stirred for 10 hours and worked up in the customary manner. The N-alkylation product ethyl 4-(1,4-benzodioxan-6-yl)-1,2-dihydro-1-(2-methoxybenzyl)-2-oxobenzofuro[3,2-b]pyridine-3-carboxylate, m.p. 105° and the O-alkylation product ethyl 4-(1,4-benzodioxan-6-yl)-2-(2-methoxybenzyloxy)benzofuro[3,2-b]pyridine-3-carboxylate, m.p. 166°, are obtained.

Sources & evidence

ORD record
ord-51f2992ea0324df6a3a36cadf17099b6
Source dataset
uspto-grants-1997_12
Patent number
US05700807

Reaction notes

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