Isopropylamine → 6-Methoxy-2-methylbenzofuran-3-carboxylic acid isopropylamide

HRID 985294Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[CH:7]=[C:8]([CH3:10])[O:9][C:5]=2[CH:4]=1.[C:13](Cl)(=[O:17])C(Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-].[CH:23]([NH2:26])([CH3:25])[CH3:24]>>[CH:23]([NH:26][C:13]([C:7]1[C:6]2[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[O:9][C:8]=1[CH3:10])=[O:17])([CH3:25])[CH3:24]

Participants

Reactant 4

HCID 6363Isopropylamine

HCID 65578Oxalyl chloride

HCID 6451240Aluminum(III) Chloride

HCID 130130736-Methoxy-2-methylbenzofuran

Product 1

HCID 207679326-Methoxy-2-methylbenzofuran-3-carboxylic acid isopropylamideYield 71%

Procedure

This material was prepared from 6-methoxy-2-methylbenzofuran 12a (500 mg, 3.1 mmole) by acylation with oxalyl chloride in the presence of AlCl3, followed by treatment with isopropylamine in a manner as previously described for example1c to give 540 mg (71%) of an off-white solid. 1H NMR (DMSO-d6) δ7.80 (1H, d, J=7.8 Hz), 7.50 (1H, d, J=8.6 Hz), 7.14 (1H, d, J=2.2 Hz), 6.89 (1H, dd, J=8.6, 2.2 Hz), 4.09 (1H, m), 3.76 (3H, s), 2.56 (3H, s), 1.16 (6H, d, J=6.6 Hz).

Sources & evidence

ORD record: ord-693e07074c63464ea6bc1488903096aa
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06869962B2

Reaction notes

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