Ethyl Acetate → 2-Methyl-benzofuran-3-carboxylic acid benzyl-(6-hydroxy-naphthalen-2ylmethyl)-amide

HRID 1357296Notes

Reaction equation

HRID 1357296 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=2[C:6]=1[C:7](Cl)=[O:8].CNCC1C=C2C(=CC=1)C=C(O)C=C2.[CH2:28]([NH:35][CH2:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][CH:46]=1)[CH:43]=[C:42]([OH:47])[CH:41]=[CH:40]2)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(OCC)(=O)C>C(Cl)Cl>[CH2:28]([N:35]([CH2:36][C:37]1[CH:46]=[CH:45][C:44]2[C:39](=[CH:40][CH:41]=[C:42]([OH:47])[CH:43]=2)[CH:38]=1)[C:7]([C:6]1[C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[O:3][C:2]=1[CH3:1])=[O:8])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 185052756-Methylaminomethyl-naphthalen-2-olHCID 185052776-(Benzylamino-methyl)-naphthalen-2-olHCID 185053172-Methylbenzofuran-3-carbonyl Chloride

Product 1

HCID 691386602-Methyl-benzofuran-3-carboxylic acid benzyl-(6-hydroxy-naphthalen-2ylmethyl)-amideYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared in the same manner as described in step 2 of Example 32, and replacing 2-ethyl-benzofuran-3-carbonyl chloride with 2-methyl-benzofuran-3-carbonyl chloride, prepared in step 2 of Example 20 and 6-methylaminomethyl-naphthalen-2-ol with 6-(benzylamino-methyl)-naphthalen-2-ol, prepared in step 3 of Example 48. Chromatography of the crude oil on 400 g silica gel (230-400 mesh) using 2-3% ethyl acetate in methylene chloride as the eluent gave 2-methyl-benzofuran-3-carboxylic acid benzyl-(6-hydroxy-naphthalen-2ylmethyl)-amide (0.71 g, 30%) as a yellow solid, mp 190-193° C.

Workup

  1. customPrepared in the same manner
  2. customprepared in step 3 of Example 48

Sources & evidence

ORD record
ord-8d67b5de4cf34390bbbef0017184f511
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

Loading…