HCID 9998689, compound → HCID 135404690, compound

HRID 1593200Notes

Reaction equation

HRID 1593200 reaction equation
C([O:8][C:9]1[CH:19]=[C:18]([O:20]CC2C=CC=CC=2)[CH:17]=[CH:16][C:10]=1[C:11](=[NH:15])[O:12][CH2:13][CH3:14])C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[OH:8][C:9]1[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:10]=1[C:11](=[NH:15])[O:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 9998689HCID 9998689, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 135404690HCID 135404690, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2,4-Dibenzyloxybenzoic acid was reacted with oxalyl chloride in toluene and DMF at 0-25° C. to give an acid chloride. The acid chloride was reacted with aqueous ammonia in methylene chloride to yield 87% (over 2 steps) of 2,4-dibenzyloxybenzamide. 2,4-Dibenzyloxybenzamide was reacted with triethyloxonium hexafluorophosphate in methylene chloride to yield 69% of ethyl 2,4-dibenzyloxybenzimidate. The ethyl 2,4-dibenzyloxybenzimidate was hydrogenated over a palladium/carbon catalyst with 1 atmosphere of hydrogen gas in ethanol, to yield 75% of ethyl 2,4-dihydroxybenzimidate. The overall yield for the reaction sequence was 34% for six steps.

Sources & evidence

ORD record
ord-86b67c41e4904e829b302295b1c8ae50
Source dataset
uspto-grants-2007_11
Patent number
US07294718B2

Reaction notes

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