Ethyl Acetate → 5-(Bis-cyclopropylmethyl-amino)-5,6-dihydro-1H,4H-imidazo[4,5,1-ij]quinolin-2-one

HRID 1648329Notes

Reaction equation

I[CH2:2][CH2:3][CH3:4].[NH2:5][CH:6]1[CH2:15][C:14]2[C:9]3=[C:10]([NH:16][C:17](=[O:18])[N:8]3[CH2:7]1)[CH:11]=[CH:12][CH:13]=2.Cl.Cl.BrC1C=[C:24]2[C:29](=[C:30]([N+]([O-])=O)[CH:31]=1)NCC(N)C2.[C:36](OCC)(=O)C>>[CH:3]1([CH2:4][N:5]([CH2:24][CH:29]2[CH2:31][CH2:30]2)[CH:6]2[CH2:15][C:14]3[C:9]4=[C:10]([NH:16][C:17](=[O:18])[N:8]4[CH2:7]2)[CH:11]=[CH:12][CH:13]=3)[CH2:36][CH2:2]1

Participants

Reactant 4

HCID 8857Ethyl Acetate

HCID 336431-Iodopropane

HCID 159377665-Amino-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

HCID 199193576-Bromo-1,2,3,4-tetrahydro-8-nitro-3-quinolinamine dihydrochloride

Product 1

HCID 157450085-(Bis-cyclopropylmethyl-amino)-5,6-dihydro-1H,4H-imidazo[4,5,1-ij]quinolin-2-one

Procedure

Following the procedure of Example 54, but substituting cyclopropylmethyl bromide for iodopropane and 5-(amino)-5,6-dihydro-4H-imidazo[4,5,1 -ij]quinolin-2(1H)-one for 6-bromo-1,2, 3,4-tetrahydro-8-nitro-3-quinolinamine dihydrochloride there were obtained 5-[bis(cyclopropylmethyl)amino]-5, 6-dihydro-4H-imidazo[4,5,1 -ij ]quinolin-2(1H)-one, mp 152-154 from ethyl acetate:hexane and 5 -(cyclopropylmethylamino)-5,6-dihydro-4H-imidazo [4,5,1 -ij]quinolin-2(1H) -one. The latter compound was converted to the hydrochloride salt, mp 309° C. from methanol:ether. ##STR2##

Sources & evidence

ORD record: ord-590a9bda83374fe2aa4b830101d0f761
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05436240

Reaction notes

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