Isopropylamine → Isopropyl(6-nitroquinolin-2-yl)amine

HRID 735191Notes

Reaction equation

HRID 735191 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].Cl[C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=2)[N:7]=1>C(O)C>[CH:1]([NH:4][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=2)[N:7]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6363Isopropylamine2×HCID 109217232-Chloro-6-nitroquinoline

Product 1

HCID 43450861Isopropyl(6-nitroquinolin-2-yl)amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.55 mL (29.96 mmol) of isopropylamine is added to a solution of 1.25 g (5.99 mmol) of 2-chloro-6-nitroquinoline in 50 mL of ethanol and the mixture is stirred for 18 hours at ambient temperature. Then the reaction mixture is heated to 65° C. in the microwave for 2 hours. The reaction mixture is then evaporated down, the residue is taken up in 20 mL of DMF, combined with 2.55 mL (29.96 mmol) of isopropylamine, and stirred for 18 hours at ambient temperature. The reaction mixture is evaporated down and the residue is combined with ethyl acetate and water. The organic phase is extracted twice with water. The aqueous phases are extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is then removed. Yield: 0.75 g (54.1% of theory); C12H13N3O2 (M=221.25); calc.: molecular ion peak (M+H)+: 232; found: molecular ion peak (M+H)+: 232; Rf value: 0.48 (silica gel, petroleum ether/ethyl acetate (2:1)).

Workup

  1. temperatureThen the reaction mixture is heated to 65° C. in the microwave for 2 hours
  2. customThe reaction mixture is then evaporated down
  3. stirringstirred for 18 hours at ambient temperature
  4. customThe reaction mixture is evaporated down
  5. extractionThe organic phase is extracted twice with water
  6. extractionThe aqueous phases are extracted twice with ethyl acetate
  7. dry with materialThe combined organic phases are dried over sodium sulfate
  8. customthe solvent is then removed

Sources & evidence

ORD record
ord-bf77665f2141422ab25de5f99800d87b
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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