Dichloromethane → Anthranilic Acid

HRID 1978916Notes

Reaction equation

HRID 1978916 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][C:8]([NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14])=[O:9])=[O:5])[CH3:2].C(N(CC)CC)C.C(Cl)[Cl:28]>>[C:13]([OH:15])(=[O:14])[C:12]1[C:11](=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH2:10].[Cl:28][C:8]([CH2:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:9]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 14296407HCID 14296407, compound

Product 2

HCID 227Anthranilic AcidHCID 84648Butanoic acid, 4-chloro-4-oxo-, ethyl ester

Procedure

In the same way as in Example 15, the intermediate 2 is reacted with 2-(3-ethoxycarbonylpropanoylamino)benzoic acid obtained by reaction of anthranilic acid with ethyl 3-chlorocarbonylpropanoate in CH2Cl2 in the presence of triethylamine, according to a method adapted from Tetrahedron Lett. 50 (1994) 34, 10331. The product is purified by flash chromatography on a column of silica, eluting with the solvent C/A30.

Sources & evidence

ORD record
ord-98354a3d052b4a5d9ccdfd8aa68d5ce4
Source dataset
uspto-grants-2001_05
Patent number
US06239130B1

Reaction notes

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