Dimethylformamide → 6-[[2-(Acetylamino)-1-oxopropyl]amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 851002

Reaction equation

HRID 851002 reaction equation
[C:1]([NH:4][C@H:5]([C:7]([OH:9])=O)[CH3:6])(=[O:3])[CH3:2].S(Cl)(Cl)=O.CN(C)C=O.[NH2:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[C:24]([C:30]([OH:32])=[O:31])[C:23]2=[O:33].C(N(CC)CC)C.Cl[Si](C)(C)C>ClCCl>[C:1]([NH:4][CH:5]([CH3:6])[C:7]([NH:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[C:24]([C:30]([OH:32])=[O:31])[C:23]2=[O:33])=[O:9])(=[O:3])[CH3:2]

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 88064N-Acetyl-L-alanineHCID 32812016-Amino-4-hydroxyquinoline-3-carboxylic acid

Product 1

HCID 131368746-[[2-(Acetylamino)-1-oxopropyl]amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1.73 g (13.2 mmol) of N-acetyl-L-alanine, 0.97 ml (13.2 mmol) of thionyl chloride, 1.02 ml (13.02 mmol) dimethylformamide, and 50 ml of dichloromethane is stirred at -20° to -30° for 20 minutes. A mixture of 2.45 g (12 mmol) of 6-amino-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 5.04 ml (36 mmol) triethylamine, 4.57 ml (36 mmol) chlorotrimethylsilane and 100 ml of dichloromethane is stirred at room temperature for 25 minutes and is cooled to -60°. The cold acid chloride solution is added to the cold silylated quinoline and is stirred for 2 hours while the temperature comes up to 10°. The reaction mixture is evaporated to dryness and the residue is treated with water to give 2.60 g of 6-[[2-(acetylamino)-1-oxopropyl]amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 196°-200° .

Workup

  1. stirringis stirred at room temperature for 25 minutes
  2. temperatureis cooled to -60°
  3. stirringis stirred for 2 hours while the temperature
  4. customcomes up to 10°
  5. customThe reaction mixture is evaporated to dryness
  6. additionthe residue is treated with water

Sources & evidence

ORD record
ord-42001e47112f4913b02a046608b59e19
Source dataset
uspto-grants-1983_05
Patent number
US04382089

Linked notes

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