Veratroyl chloride → HCID 71208627, compound

HRID 1887881Notes

Reaction equation

HRID 1887881 reaction equation
[NH2:1][CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([Cl:14])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:4]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[C:26](Cl)=[O:27].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:14][C:8]1[CH:7]=[C:6]2[C:11]([C:12](=[O:13])[C:3]([CH2:2][NH:1][C:26](=[O:27])[C:25]3[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:23]([O:22][CH3:21])[CH:24]=3)=[CH:4][N:5]2[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 77070Veratroyl chlorideHCID 81531DiisopropylethylamineHCID 712083983-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one2×

Product 1

HCID 71208627HCID 71208627, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a 200 mL round-bottomed flask, 3-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one (intermediate D) (25 mg, 0.088 mmol) and 3,4-dimethoxybenzoyl chloride (17.6 mg, 0.088 mmol) were combined with methylene chloride (3 mL) to give a yellow suspension. The reaction mixture was cooled to 0° C. After 15 min. stirring at reduced temperature, N,N-diisopropylethylamine (56.7 mg, 76.6 μL, 0.439 mmol) was added. The reaction mixture quickly became a yellow solution, then was stirred at 0° C. for 1 hr. After this time, LC/MS indicated that the reaction was complete. The reaction mixture was warmed to room temperature, then stirred overnight. In the morning, the reaction mixture was concentrated over silica gel. Flash chromatography (25 gram Analogix column, 20% ethyl acetate-hexanes ramped to 100% ethyl acetate) was used to purify the product. N-(7-Chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-3,4-dimethoxy-benzamide (26 mg, 59%) was obtained as a white solid. MS calcd. for C25H21ClN2O4 [(M+H)+] 448.9, obsd. 449.1.

Workup

  1. customto give a yellow suspension
  2. additionwas added
  3. temperatureThe reaction mixture was warmed to room temperature
  4. stirringstirred overnight
  5. concentrationIn the morning, the reaction mixture was concentrated over silica gel
  6. customto purify the product

Sources & evidence

ORD record
ord-9a827b46d4f74e2d96ef844fd7f88ff2
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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