Pyridine → HCID 67646535, compound

HRID 964731Notes

Reaction equation

HRID 964731 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[N+:8]([C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1)([O-])=O.N1C=CC=CC=1>C(O)C>[NH2:8][C:11]1[CH:19]=[CH:18][C:14]([C:15]([N:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH2:1])[CH2:3]2)=[O:16])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 85024-Nitrobenzoyl chlorideHCID 100093-Aminopyridine

Product 1

HCID 67646535HCID 67646535, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Aminopyridine, 60, is first reacted with 4-nitrobenzoyl chloride in the presence of pyridine at 80° C. (step 1) and the product, 62, is subsequently hydrogenated in the presence of ethanol (step 2) to give N-(p-aminobezoyl) -3-aminopyridine, 64. In a separate reaction, 2,5-dimethyl-1,4-phenylenediamine, 66, is converted to 2,5-dimethyl-1,4-dinitrobenzene in a "reverse" Sandmeyer reaction with isoamyl nitrite and acetic acid (step 3), and subsequently treated with copper sulfate in the presence of sodium nitrite (step 4) to produce the intermediate, 68. This intermediate, 68, is oxidized with CrO3 and chlorinated with SOCl2 (step 5) to give 2,5-dinitroterephthaloyl chloride 70. One equivalent of N-(p-aminobezoyl)-3-aminopyridine, 64, and 0.5 equivalent of 2,5-dinitroterephthaloyl chloride, 70, are reacted in pyridine (step 6) to produce a bis-anilide derivative of 2,5-dinitroterephthaloyl chloride 72, and the product is again hydrogenated and activated with isoamyl nitrite (step 7) to yield the final activated product 74.

Sources & evidence

ORD record
ord-9474ba24bc59421e9e91497f7c624400
Source dataset
uspto-grants-1998_06
Patent number
US05770736

Reaction notes

Loading…