Acetyl chloride → HCID 9821261, compound

HRID 611983Notes

Reaction equation

HRID 611983 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].[NH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][C:17]([C:23]#[N:24])=[C:16]2[NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Br:32])[CH:27]=1>C(Cl)Cl.O1CCCC1>[Br:32][C:28]1[CH:27]=[C:26]([NH:25][C:16]2[C:15]3[C:20](=[CH:21][CH:22]=[C:13]([NH:12][C:8](=[O:10])[CH3:9])[CH:14]=3)[N:19]=[CH:18][C:17]=2[C:23]#[N:24])[CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrile

Product 1

HCID 9821261HCID 9821261, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Triethylamine (0.359 g, 3.55 mmol) and acetyl chloride (0.277 mg, 3.55 mmol) were added to an ice cold solution of 1.00 g (2.96 mmol) of 6-amino-4-[(3-bromophenyl)-amino]-3-quinolinecarbonitrile in 8 mL of methylene chloride and 6 mL of tetrahydrofuran under N2. After stirring overnight at 25° C., volatile material was removed, and the residue was slurried with water and collected. Recrystallization from ethanol gave 0.543 g of brown solid; mp 258-261° C.(dec).

Workup

  1. customvolatile material was removed
  2. customcollected
  3. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-98cb945b98ef40ac8eb31141c578748f
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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