t-Butyl (1,2,5,6-tetrahydro-2-oxo-4H-imidazo(4,5,1-ij)quinolin-5-yl)carbamate → 5-Amino-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

HRID 327458Notes

Reaction equation

HRID 327458 reaction equation
[O:1]=[C:2]1[N:12]2[C:13]3[C:8]([CH2:9][CH:10]([NH:14]C(=O)OC(C)(C)C)[CH2:11]2)=[CH:7][CH:6]=[CH:5][C:4]=3[NH:3]1>Cl.CO>[NH2:14][CH:10]1[CH2:9][C:8]2[C:13]3=[C:4]([NH:3][C:2](=[O:1])[N:12]3[CH2:11]1)[CH:5]=[CH:6][CH:7]=2

Participants

3

Reactant 1

HCID 15937764t-Butyl (1,2,5,6-tetrahydro-2-oxo-4H-imidazo(4,5,1-ij)quinolin-5-yl)carbamate

Product 1

HCID 159377665-Amino-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-oneYield 12%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

t-Butyl (1,2,5,6-tetrahydro-2-oxo-4H-imidazo(4,5,1-ij)quinolin-5-yl)carbamate (1.65 g, 0.057 mol) was dissolved in methanol HCl (85 mL) and stirred at room temperature for 1 hour. The solvent was removed under reduced pressure to give 1.29 g of crude product. An analytical sample was recrystallized from methanol and ether to give a pink solid, mp >300° C. Anal. Calcd. for C10H11N3O.HCl.1/2H2O: C, 51.58; H, 5.58; Cl, 15.11; N, 17.90. Found: C, 51.04; H, 5.47; Cl, 15.10; N, 17.86.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a594b919e6904ae999dc1fac777f2fae
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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