Ethyl orthopropionate → 8-benzyloxy-2-ethyl-1-methyl-1H-imidazo[4,5-c]quinoline

HRID 598305Notes

Reaction equation

HRID 598305 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([NH2:19])=[C:12]2[NH:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22](OC1C=C2C(C(NCCOC3C=CC=CC=3)=C(N)C=N2)=CC=1)[C:23]1C=CC=CC=1.[C:51](OCC)(OCC)(OCC)CC.C(OC)(OC)(OC)CCCC>>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[CH:14][C:13]3[N:19]=[C:21]([CH2:22][CH3:23])[N:20]([CH3:51])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 66995Ethyl orthopropionateHCID 83755Trimethyl orthovalerateHCID 670509287-benzyloxy-N4-(2-phenoxyethyl)quinoline-3,4-diamineHCID 670510076-(benzyloxy)-N4-methylquinoline-3,4-diamine

Product 1

HCID 670509308-benzyloxy-2-ethyl-1-methyl-1H-imidazo[4,5-c]quinoline

Procedure

The general method described in Part A of Example 47 was followed using 6-benzyloxy-N4-methylquinoline-3,4-diamine (7.91 g, 28.3 mmol) in lieu of 7-benzyloxy-N4-(2-phenoxyethyl)quinoline-3,4-diamine and triethyl orthopropionate (12.69 mL, 56.6 mmol) in lieu of trimethyl orthovalerate. The precipitate from the reaction was isolated in two crops to provide 7.56 g of 8-benzyloxy-2-ethyl-1-methyl-1H-imidazo[4,5-c]quinoline as a yellow solid, mp 168.2-169.0° C.

Workup

  1. customThe precipitate from the reaction was isolated in two crops

Sources & evidence

ORD record
ord-7968087d827041948e5b0df4489bc3d7
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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