Chlorotrimethylsilane → 8-[[2-(Acetylamino)-1-oxopropyl]amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 851008

Reaction equation

HRID 851008 reaction equation
[C:1]([NH:4][C@H:5]([C:7]([OH:9])=O)[CH3:6])(=[O:3])[CH3:2].CN1CCOCC1.ClC(OC)=O.[NH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]2[C:32]=1[NH:31][CH:30]=[C:29]([C:33]([OH:35])=[O:34])[C:28]2=[O:36].C(N(CC)CC)C.Cl[Si](C)(C)C>ClCCl.C(#N)C>[C:1]([NH:4][CH:5]([CH3:6])[C:7]([NH:22][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]2[C:32]=1[NH:31][CH:30]=[C:29]([C:33]([OH:35])=[O:34])[C:28]2=[O:36])=[O:9])(=[O:3])[CH3:2]

Participants

9

Reactant 6

HCID 6397ChlorotrimethylsilaneHCID 6586Methyl chloroformateHCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 88064N-Acetyl-L-alanineHCID 128663498-Amino-4-hydroxyquinoline-3-carboxylic acid

Product 1

HCID 131368788-[[2-(Acetylamino)-1-oxopropyl]amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 47.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.93 g (30 mmol) of N-acetyl-L-alanine, 3.3 ml (30 mmol) of N-methyl morpholine, 2.33 ml (30 mmol) of methyl chloroformate, and 80 ml of acetonitrile is stirred at -10° to -20° for 30 minutes. A mixture of 4.08 g (20 mmol) of 8-amino-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 8.4 ml (60 mmol) of triethylamine, 7.6 ml (60 mmol) of chlorotrimethylsilane, and 100 ml of dichloromethane was stirred at room temperature for 40 minutes and then cooled to -20°. The cold mixed anhydride is added to the cold silylated quinoline and stirred for 4 hours with cooling and overnight at room temperature. The reaction mixture is evaporated to dryness and the residue is treated with acetonitrile and 1N hydrochloric acid. The solid is filtered to give 3.03 g of 8-[[2-(acetylamino)-1-oxopropyl]amino]-1,4-dihydro-4 -oxo-3-quinolinecarboxylic acid.

Workup

  1. stirringwas stirred at room temperature for 40 minutes
  2. temperaturecooled to -20°
  3. stirringstirred for 4 hours
  4. customThe reaction mixture is evaporated to dryness
  5. additionthe residue is treated with acetonitrile and 1N hydrochloric acid
  6. filtrationThe solid is filtered

Sources & evidence

ORD record
ord-aefc5b7aaa064d9894f82adf7b1a2ce8
Source dataset
uspto-grants-1983_05
Patent number
US04382089

Linked notes

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