Triethylamine → 1-[(6-Bromo-3-nitroquinolin-4-yl)amino]-2-methylpropan-2-ol

HRID 244860Notes

Reaction equation

HRID 244860 reaction equation
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][C:11]([N+:17]([O-:19])=[O:18])=[C:10]2O.C(N(CC)CC)C.[NH2:28][CH2:29][C:30]([CH3:33])([OH:32])[CH3:31]>CN(C)C=O.O1CCCC1.O>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][C:11]([N+:17]([O-:19])=[O:18])=[C:10]2[NH:28][CH2:29][C:30]([CH3:33])([OH:32])[CH3:31]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 951022-Propanol, 1-amino-2-methyl-HCID 178526759HCID 178526759, compound

Product 1

HCID 690795671-[(6-Bromo-3-nitroquinolin-4-yl)amino]-2-methylpropan-2-olYield 90.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

Phosphorous oxychloride (5.45 mL, 58.5 mmol) was added to a slurry of 6-bromo-3-nitroquinolin-4-ol (15 g, 55.7 mmol) in N,N-dimethylformamide (100 mL). The reaction mixture was heated to 100° C. for 10 minutes and then cooled to ambient temperature. The solution was poured into ice water (400 mL) and stirred for 20 minutes. The resulting precipitate was filtered, washed with water, and dried. The recovered solid was transferred to a round bottomed flask and tetrahydrofuran (100 mL) was added. A solution of triethylamine (11.6 mL, 83.5 mmol) and 1-amino-2-methylpropan-2-ol (5.21 g, 58.5 mmol) in tetrahydrofuran (20 mL) was added dropwise. The reaction was stirred for 16 hours. The mixture was poured into water and stirred for 15 minutes. The resulting yellow solid was filtered and dried to provide 17.2 g of 1-[(6-bromo-3-nitroquinolin-4-yl)amino]-2-methylpropan-2-ol as a yellow solid.

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried
  5. customThe recovered solid was transferred to a round bottomed flask
  6. additiontetrahydrofuran (100 mL) was added
  7. stirringThe reaction was stirred for 16 hours
  8. stirringstirred for 15 minutes
  9. filtrationThe resulting yellow solid was filtered
  10. customdried

Sources & evidence

ORD record
ord-7bb46d0d6a264e188e728b1f86290709
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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