Benzene → 4-[(2-Methyl-hydrazino)-methyl]-benzoic acid furfurylamide

HRID 1579704Notes

Reaction equation

HRID 1579704 reaction equation
C[N:2]([C:24](OCC1C=CC=CC=1)=O)[N:3]([CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)C(OCC1C=CC=CC=1)=O.[CH2:34]([NH2:40])[C:35]1[O:39][CH:38]=[CH:37][CH:36]=1.N1C=CC=CC=1.C1C=CC=CC=1>CO.[C].[Pd]>[CH2:34]([NH:40][C:19](=[O:20])[C:18]1[CH:17]=[CH:16][C:15]([CH2:14][NH:3][NH:2][CH3:24])=[CH:23][CH:22]=1)[C:35]1[O:39][CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 1049PyridineHCID 3438FurfurylamineHCID 215690594-[(2-Methyl-1,2-dicarbobenzoxy-hydrazino)-methyl]-benzoyl chloride

Product 1

HCID 541899654-[(2-Methyl-hydrazino)-methyl]-benzoic acid furfurylamide

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

By reaction of 23.4 g. of 4-[(2-methyl-1,2-dicarbobenzoxyhydrazino)-methyl]-benzoyl chloride with 4.85 g. of furfurylamine in a mixture of 8 ml. pyridine and 50 ml. of benzene according to the procedure of Example 4 above, followed by hydrogenolysis of the condensation product with palladium-carbon in methanol, there was obtained 4-[(2-methyl-hydrazino)-methyl]-benzoic acid furfurylamide, the oxalate of which melted at 170°-171° (dec.).

Workup

  1. customBy reaction of 23.4 g

Sources & evidence

ORD record
ord-3f7227782f1943e9a37bf14159e53e62
Source dataset
uspto-grants-1976_01
Patent number
US03931268

Reaction notes

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