Ethyl orthoformate → HCID 22320531, compound

HRID 433199Notes

Reaction equation

HRID 433199 reaction equation
[C:1]1([S:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][C:15]=2[NH2:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:25](OCC)(OCC)OCC.Cl.N1C=CC=CC=1>>[C:1]1([S:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[C:14]3[C:23]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[N:17]=[CH:16][C:15]=3[N:24]=[CH:25]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 31214Ethyl orthoformateHCID 10176127Pyridinium chlorideHCID 86588279HCID 86588279, compound

Product 1

HCID 22320531HCID 22320531, compound

Procedure

Using the general method of Example 1 Part D, N4-[5-(phenylthio)pentyl]quinoline-3,4-diamine (5.1 g, 15.1 mmol) was cyclized using triethyl orthoformate (2.46 g, 16.6 mmol) in the presence of a catalytic amount of pyridine hydrochloride to provide 1-[5-(phenylthio)pentyl]-1H-imidazo[4,5-c]quinoline as a yellow solid.

Sources & evidence

ORD record
ord-77d85c2b3e344714b8969e8695d79843
Source dataset
uspto-grants-2003_12
Patent number
US06667312B2

Reaction notes

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