Triethylamine → HCID 178476494, compound

HRID 389065Notes

Reaction equation

HRID 389065 reaction equation
C(N(CC)CC)C.[Cl-].[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([OH:21])=[C:15]([NH3+:20])[CH:16]=[N:17]2)=[CH:12][CH:11]=1.[C:22]([O:25][CH2:26][C:27](Cl)=[O:28])(=[O:24])[CH3:23]>ClCCl>[C:22]([O:25][CH2:26][C:27]([NH:20][C:15]1[CH:16]=[N:17][C:18]2[C:13]([C:14]=1[OH:21])=[CH:12][CH:11]=[C:10]([Br:9])[CH:19]=2)=[O:28])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 178479575HCID 178479575, compound

Product 1

HCID 178476494HCID 178476494, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (161 g, 1.59 mol) was added to a suspension of 7-bromo-4-hydroxyquinolin-3-aminium chloride (224 g, 0.815 mol) in dichloromethane (2.25 L), and the mixture was cooled to approximately 0° C. Acetoxyacetyl chloride (112 g, 0.820 mol) was added over a period of one hour. The reaction was stirred at room temperature for one hour and then allowed to stand for three days. A solid was present and was isolated by filtration and pressed dry. The solid was stirred in deionized water (2 L) for two hours, isolated by filtration, dried overnight on the filter funnel, and further dried in a vacuum oven at 60 to 70° C. to provide 223 g of 2-[(7-bromo-4-hydroxyquinolin-3-yl)amino]-2-oxoethyl acetate as a reddish brown solid.

Workup

  1. waitto stand for three days
  2. customwas isolated by filtration
  3. custompressed dry
  4. stirringThe solid was stirred in deionized water (2 L) for two hours
  5. customisolated by filtration
  6. customdried overnight on the filter funnel
  7. customfurther dried in a vacuum oven at 60 to 70° C.

Sources & evidence

ORD record
ord-bd99314307394bf7bbffa1c601484259
Source dataset
uspto-grants-2013_02
Patent number
US08378102B2

Reaction notes

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