Water → N-benzoyl-1,2-dihydroquinolin-4(3H)-one

HRID 1097782Notes

Reaction equation

HRID 1097782 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:20])[CH2:12][CH2:11]1.C(N(CC)CC)C.O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:20])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 1171582,3-dihydroquinolin-4(1H)-one

Product 1

HCID 283524N-benzoyl-1,2-dihydroquinolin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (0.30 ml, 2.58 mmol) is added dropwise to a solution of 2,3-dihydro-1H-quinolin-4-one (260 mg, 1.77 mmol), triethylamine (0.32 ml, 2.30 mmol) and DMAP (10 mg) in CH2Cl2 at 0° C. The resulting mixture is stirred at room temperature for overnight. Water is added and the mixture is extracted with CH2Cl2 and washed with brine, dried over anhydrous sodium sulfate. After concentration, a residue is yielded, which is used “as is” for the next reaction without further purification.

Workup

  1. extractionthe mixture is extracted with CH2Cl2
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationAfter concentration
  5. customa residue is yielded
  6. customfor the next reaction
  7. customwithout further purification

Sources & evidence

ORD record
ord-41fbb5f15529470e89a6d273338dcc69
Source dataset
uspto-grants-2012_03
Patent number
US08143278B2

Reaction notes

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