Ethyl Acetate → trans-1-(4-Methoxy-2-hydroxymethylanilino)-2-ethoxycarbonylaminoindane

HRID 980508Notes

Reaction equation

HRID 980508 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH2:4][OH:5].Cl[C@@H:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][C@H:14]1[NH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[Ba+2].C(OCC)(=O)C>CN(C)C=O>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:2]([NH:1][C@@H:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][C@H:14]2[NH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:3]([CH2:4][OH:5])[CH:6]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10563Barium CarbonateHCID 7070371trans-1-Chloro-2-ethoxycarbonylaminoindaneHCID 13756678(2-Amino-5-methoxyphenyl)methanol

Product 1

HCID 54338086trans-1-(4-Methoxy-2-hydroxymethylanilino)-2-ethoxycarbonylaminoindaneYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-amino-5-methoxybenzyl alcohol (5 g; 32.7 m.mol) and trans-1-chloro-2-ethoxycarbonylaminoindane (7.83 g; 32.7 m.mol) in dimethylformamide (80 ml) was treated with barium carbonate (3.37 g; 17 m.mol) in a manner similar to that in Description 3 to give the title compound (5.1 g; 44%), m.p. 142°-144° (from ethyl acetate).

Sources & evidence

ORD record
ord-0fec37ce11ae4e1f907027a22e157250
Source dataset
uspto-grants-1987_01
Patent number
US04638066

Reaction notes

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