Methanol → 1-(2-Chloroethyl)-3-quinolin-4-yl-urea

HRID 2223698Notes

Reaction equation

HRID 2223698 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Cl:12][CH2:13][CH2:14][N:15]=[C:16]=[O:17].CO>C1COCC1>[Cl:12][CH2:13][CH2:14][NH:15][C:16]([NH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1)=[O:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 160352-Chloroethyl isocyanateHCID 684764-Aminoquinoline

Product 1

HCID 226433981-(2-Chloroethyl)-3-quinolin-4-yl-urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-aminoquinoline (3.46 g, 24 mmol) in dry THF is added chloroethylisocyanate (3.1 mL, 36 mmol). The reaction mixture is stirred for 18 h. MeOH (10 mL) is added, and stirring is continued for an additional hour. The reaction mixture is evaporated, and partitioned between DCM and aqueous 5% citric acid (150 mL). The aqueous layer is carefully adjusted to pH 9 with solid NaHCO3. The precipitate is filtered, washed with H2O (5×20 mL) and Et2O (2×20 mL), and dried in vacuo at 45° C. to provide the title compound.

Workup

  1. stirringstirring
  2. waitis continued for an additional hour
  3. customThe reaction mixture is evaporated
  4. custompartitioned between DCM and aqueous 5% citric acid (150 mL)
  5. filtrationThe precipitate is filtered
  6. washwashed with H2O (5×20 mL) and Et2O (2×20 mL)
  7. customdried in vacuo at 45° C.

Sources & evidence

ORD record
ord-b0bf2e0a4f594f2b8b542ef67fb33288
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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