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

HRID 327486Notes

Reaction equation

ICCC.[NH2:5][CH:6]1[CH2:15][C:14]2[C:9]3=[C:10]([N:16]=[CH:17][N:8]3[CH2:7]1)[CH:11]=[CH:12][CH:13]=2.N1[C:27]2[C:22](=CC=[CH:25][CH:26]=2)C=CC1=O.Cl.Cl.BrC1C=[C:34]2[C:39](=[C:40]([N+]([O-])=O)[CH:41]=1)NCC(N)C2.C(OCC)(=[O:48])C>>[CH:40]1([CH2:41][N:5]([CH2:22][CH:27]2[CH2:26][CH2:25]2)[CH:6]2[CH2:15][C:14]3[C:9]4=[C:10]([NH:16][C:17](=[O:48])[N:8]4[CH2:7]2)[CH:11]=[CH:12][CH:13]=3)[CH2:34][CH2:39]1

Participants

Reactant 5

HCID 60382-Hydroxyquinoline

HCID 8857Ethyl Acetate

HCID 336431-Iodopropane

HCID 152919495-(amino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin

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(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. (dec) from methanol:ether. ##STR2##

Sources & evidence

ORD record: ord-0f3111c5df0e439d9772832383efe0ad
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05273975

Reaction notes

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