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

HRID 1648299Notes

Reaction equation

HRID 1648299 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][CH2:9][CH:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:7]2.[C:20](Cl)(Cl)=[O:21].CN>C1COCC1>[O:21]=[C:20]1[N:10]2[C:11]3[C:6]([CH2:7][CH:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])[CH2:9]2)=[CH:5][CH:4]=[CH:3][C:2]=3[NH:1]1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 6371PhosgeneHCID 19108500t-Butyl (8-amino-1,2,3,4-tetrahydro-3-quinolyl)carbamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

t-Butyl (8-amino-1,2,3,4-tetrahydro-3-quinolyl)carbamate (2.70 g) was dissolved in THF (100 mL) and stirred while a solution of phosgene in THF (20.7 mL of 0.40 M, 0.093 mol) was added. After 5 minutes, methylamine (2.08 g, 0.020 mol) was added and the solution stirred for an additional 10 minutes. The THF was removed under reduced pressure and the material was partitioned between chloroform (250 mL) and water (20 nil,). The chloroform was washed with 4N sodium hydroxide (5 mL) and evaporated. The crude material was combined with that of an earlier reaction (0.002 mol scale) and purified by chromatography on silica gel in 1% methanol: chloroform to give 2.28 g of product. Crystallization from methanol:ether (1:1) gave 1.60 g (54%) white solid, mp 235°-36° C. Anal. Calc'd for C15H19N3O3 : C, 62.26; H, 6.62; N, 14.52. Found: C, 61.65; H, 6.94; N, 14.23.

Workup

  1. additionwas added
  2. customThe THF was removed under reduced pressure
  3. customthe material was partitioned between chloroform (250 mL) and water (20 nil,)
  4. washThe chloroform was washed with 4N sodium hydroxide (5 mL)
  5. customevaporated
  6. customof an earlier reaction (0.002 mol scale)
  7. custompurified by chromatography on silica gel in 1% methanol

Sources & evidence

ORD record
ord-68fa5fcc34434be0ac0d60429fda00ba
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

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