Water → HCID 21092961, compound

HRID 1785930Notes

Reaction equation

HRID 1785930 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:11][CH:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)=[O:20].C(N(C(C)C)CC)(C)C.[C:39](Cl)(=[O:41])[CH3:40].O>C(Cl)Cl>[CH3:28][O:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[C:19]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]([N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:39](=[O:41])[CH3:40])[CH2:11][C:2]1([CH3:29])[CH3:1])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 21092855HCID 21092855, compound

Product 1

HCID 21092961HCID 21092961, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2,2-dimethyl-4-phenylamino-3,4-dihydro-2H-quinolin-1-yl)-(3-methoxy-phenyl)-methanone in methylene chloride (5 mL) was added diisopropylethylamine followed by acetyl chloride. The mixture was stirred at room temperature over night. The mixture was poured into water and extracted with dichloromethane. The extracts were washed with 1 M (aq) NaOH and brine, dried over magnesium sulfate, filtered, dried and concentrated. The crude residue was purified by silica gel chromatography (50% hexanes/50% ethyl acetate) to afford N-[1-(3-methoxy-benzoyl)-2,2-dimethyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-acetamide.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extracts were washed with 1 M (aq) NaOH and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customdried
  6. concentrationconcentrated
  7. customThe crude residue was purified by silica gel chromatography (50% hexanes/50% ethyl acetate)

Sources & evidence

ORD record
ord-742d5628a0184da99e04baf470b05eb8
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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