Hydrochloric Acid → HCID 20454283, compound

HRID 1461963Notes

Reaction equation

HRID 1461963 reaction equation
[CH2:1]([N:8]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:9](=[O:27])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:12]([N+:24]([O-])=O)[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.Cl>O>[NH2:24][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:9]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 20454279HCID 20454279, compound

Product 1

HCID 20454283HCID 20454283, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

By reducing N,N-dibenzyl-4-benzyloxy-3-nitrobenzamide (melting point 131°-132° C.) in water-containing methanol with reduced iron powder-hydrochloric acid, 3-amino-N,N-dibenzyl-4-benzyloxybenzamide (melting point 81° C.) was obtained. Then, by reacting 3-amino-N,N-dibenzyl-4-benzyloxybenzamide with ethyl oxalyl chloride in the presence of pyridine in tetrahydrofuran, ethyl 2-benzyloxy-5-(N,N-dibenzylcarbamoyl)oxanilate (melting point 132°-133° C.) was obtained. A solution of 3.6 g of ethyl 2-benzyloxy-5-(N,N-dibenzylcarbamoyl)oxanilate thus obtained in 100 ml of ethanol was catalytically hydrogenated in the presence of 0.8 g of 10% palladium carbon until the absorption of hydrogen stopped. After the reaction was over, the catalyst was filtered off and the filtrate was concentrated under reduced pressure to provide 2.7 g of ethyl 5-(N,N-dibenzylcarbamoyl)-2-hydroxyoxanilate, a gum.

Sources & evidence

ORD record
ord-4ccebc7f7d194b32bc50d687b87d6425
Source dataset
uspto-grants-1984_07
Patent number
US04457872

Reaction notes

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