Water → HCID 21092960, compound

HRID 1349579Notes

Reaction equation

HRID 1349579 reaction equation
[C:1]1([NH:7][CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([C:18]([C:20]3[CH:25]=[CH:24][C:23](OC)=[CH:22][CH:21]=3)=[O:19])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N([CH:34]([CH3:36])C)CC)(C)C.[C:37](Cl)(=[O:39])C.[OH2:41]>C(Cl)Cl>[CH3:37][O:39][C:24]1[CH:25]=[C:20]([CH:21]=[CH:22][CH:23]=1)[C:18]([N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]([N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:34](=[O:41])[CH3:36])[CH2:9][CH2:10]1)=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 21092944HCID 21092944, compound

Product 1

HCID 21092960HCID 21092960, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-phenylamino-3,4-dihydro-2H-quinolin-1-yl)-(4-methoxy-phenyl)-methanone in methylene chloride 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)-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-fa5504dad8ef49fe982ef063db8edbe3
Source dataset
uspto-grants-2007_05
Patent number
US07211672B2

Reaction notes

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