Quinaldic Acid → HCID 43390419, compound

HRID 2384525Notes

Reaction equation

HRID 2384525 reaction equation
[C:1]([OH:13])(=O)[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.CN1CCOCC1.C(OC(Cl)=O)C(C)C.[CH3:29][C:30]([NH2:34])([CH3:33])[CH2:31][OH:32]>C(Cl)Cl>[OH:32][CH2:31][C:30]([NH:34][C:1]([C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)=[O:13])([CH3:33])[CH3:29]

Participants

6

Reactant 4

HCID 7124Quinaldic AcidHCID 79724-MethylmorpholineHCID 118072-Amino-2-methyl-1-propanolHCID 62365Isobutyl chloroformate

Product 1

HCID 43390419HCID 43390419, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an oven dried 250 mL round bottomed flask was weighed quinaldic acid (866 mg, 5.0 mmol). A magnetic stir bar was added and the flask was put under N2 atmosphere. The flask was charged with DCM (50 mL) and cooled to 0° C. in an ice bath. The flask was charged with N-methyl morpholine (720 μL, 7.5 mmol) and isobutlychloroformate (752 μL, 5.75 mmol) via syringe addition. The reaction was allowed to stir at 0° C. for 10 min until the solution became cloudy. At which point 2-methyl-2-aminopropanol (550 uL, 5.75 mmol) was added slowly to the flask via syringe. The reaction mixture was allowed to slowly warm to room temperature. The reaction was quenched after 2 h with 1M HCl solution (30 mL) and transferred to a separatory funnel with DCM (50 mL). The layers were partitioned and the organic phase was washed with H2O (2×30 mL) and brine (1×40 mL). After drying over Na2SO4 and filtration, the mixture was concentrated under reduced pressure. The crude mixture was purified by flash chromatography eluting with a 1:1 mixture of EtOAc and hexanes to afford N-(1-hydroxy-2-methylpropan-2-yl)quinoline-2-carboxamide as a colorless oil in 91% yield (1.112 g, 4.55 mmol) according to the following reaction

Workup

  1. customTo an oven dried 250 mL round bottomed flask
  2. additionA magnetic stir bar was added
  3. additionaddition
  4. temperatureto slowly warm to room temperature
  5. customThe reaction was quenched after 2 h with 1M HCl solution (30 mL)
  6. customtransferred to a separatory funnel with DCM (50 mL)
  7. customThe layers were partitioned
  8. washthe organic phase was washed with H2O (2×30 mL) and brine (1×40 mL)
  9. dry with materialAfter drying over Na2SO4 and filtration
  10. concentrationthe mixture was concentrated under reduced pressure
  11. customThe crude mixture was purified by flash chromatography
  12. washeluting with a 1:1 mixture of EtOAc and hexanes

Sources & evidence

ORD record
ord-210768e339cc494d8c66a9ad7ab0e019
Source dataset
uspto-grants-2012_09
Patent number
US08263774B2

Reaction notes

Loading…