Hydrochloric Acid → 4-Quinolinamine, 2-chloro-N-(2-methylpropyl)-3-nitro-

HRID 1901956Notes

Reaction equation

HRID 1901956 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[CH3:23][CH:24]([CH3:27])[CH2:25][NH2:26].Cl>CN(C)C=O>[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]([NH:26][CH2:25][CH:24]([CH3:27])[CH3:23])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6558IsobutylamineHCID 8471TriethylamineHCID 27851382,4-Dichloro-3-nitroquinoline

Product 1

HCID 109348134-Quinolinamine, 2-chloro-N-(2-methylpropyl)-3-nitro-Yield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2,4-dichloro-3-nitroquinoline (100 g) and N,N-dimethylformamide (180 mL) was stirred, and triethylamine (42 g, 4 eq) was added dropwise, followed by dropwise addition of 2-methylpropylamine (21.5 g, 0.7 eq). The mixture was stirred at room temperature until the reaction was completed as determined by gas chromatography. Aqueous hydrochloric acid (250 mL, 4N) was added with stirring. The resulting mixture was stirred and cooled to about 0° C. to precipitate the product. The precipitate was filtered, washed with water, and dried at reduced pressure to afford the product 2-chloro-N-(2-methylpropyl)-3-nitro-4-quinolinamine in about 90% yield.

Workup

  1. stirringThe mixture was stirred at room temperature until the reaction
  2. stirringwith stirring
  3. stirringThe resulting mixture was stirred
  4. customto precipitate the product
  5. filtrationThe precipitate was filtered
  6. washwashed with water
  7. customdried at reduced pressure

Sources & evidence

ORD record
ord-378c13599e3745bc894eb58362d9a544
Source dataset
uspto-grants-1996_11
Patent number
US05578727

Reaction notes

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