Acetic Anhydride → 5-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 979467Notes

Reaction equation

HRID 979467 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([F:23])[C:11]([F:22])=[C:12]([F:21])[C:13]=2[NH:17]C(=O)C)[N:8]([CH:24]2[CH2:26][CH2:25]2)[CH:7]=1)=[O:5])C.C(OC(=O)CC(=O)C1C(F)=C(F)C(F)=C(F)C=1NC(=O)C)C.C(OC(OCC)OCC)C.C(OC(=O)C)(=O)C>>[CH:24]1([N:8]2[C:9]3[C:14](=[C:13]([NH2:17])[C:12]([F:21])=[C:11]([F:22])[C:10]=3[F:23])[C:15](=[O:16])[C:6]([C:4]([OH:5])=[O:3])=[CH:7]2)[CH2:25][CH2:26]1

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 54420809HCID 54420809, compoundHCID 54477637HCID 54477637, compound

Product 1

HCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Procedure

This product can be converted to 5-acetylamino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl ester by a three step reaction. The 2-acetylamino-3,4,5,6-tetrafluoro-β-oxobenzene-propanoic acid ethyl ester is first treated with triethylorthoformate and acetic anhydride. After removal of the solvent the residue is treated with a solution of cyclopropylamine in t-butanol. After the reaction is complete a solution of potassium t-butoxide in t-butanol is added. The resulting product is 5-acetylamino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl ester. The ester is hydrolyzed to form 1-cyclopropyl-5-amino-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.

Workup

  1. customAfter removal of the solvent the residue
  2. additionis treated with a solution of cyclopropylamine in t-butanol
  3. additionis added

Sources & evidence

ORD record
ord-38fbd81a9a2c4463aa338913ef5f91f9
Source dataset
uspto-grants-1987_05
Patent number
US04668680

Reaction notes

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