Hydrochloric Acid → HCID 69995934, compound

HRID 963389Notes

Reaction equation

HRID 963389 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:26])=[C:11]([C:14]4[CH:19]=[C:18]([CH:20]=O)[CH:17]=[C:16]([O:22][CH3:23])[C:15]=4[O:24][CH3:25])[CH:12]=3)[C:7](=[O:27])[C:6]([C:28]([OH:30])=[O:29])=[CH:5]2)[CH2:3][CH2:2]1.[NH:31]([CH2:38][CH2:39][C:40]#[N:41])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CC([O-])(C)C.[K+].Cl>CS(C)=O.O>[C:40]([C:39](=[CH:38][NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:20][C:18]1[CH:17]=[C:16]([O:22][CH3:23])[C:15]([O:24][CH3:25])=[C:14]([C:11]2[CH:12]=[C:13]3[C:8]([C:7](=[O:27])[C:6]([C:28]([OH:30])=[O:29])=[CH:5][N:4]3[CH:1]3[CH2:2][CH2:3]3)=[CH:9][C:10]=2[F:26])[CH:19]=1)#[N:41]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 141003-AnilinopropionitrileHCID 19081730HCID 19081730, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 69995934HCID 69995934, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A suspension of 310 mg of 1-cyclopropyl-6-fluoro-7-(5-formyl-2,3-dimethoxy-phenyl)-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (Example 8a)) in 3 ml of dimethyl sulphoxide is treated with 110 mg of 3-anilinopropionitrile and 185 mg of potassium tert-butylate. The resulting solution is stirred at room temperature for one hr. The reaction mixture is poured into 30 ml of water, adjusted to pH 5 with 2N aqueous HCl and extracted twice with 50 ml of methylene chloride each time. The combined organic phases are washed with 50 ml of water and with 50 ml of saturated, aqueous sodium chloride solution, dried over magnesium sulphate and concentrated. 400 mg (98%) of 7-[5-(2-cyano-3-phenylamino-allyl)-2,3-dimethoxy-phenyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid are obtained as a yellow foam.

Workup

  1. extractionextracted twice with 50 ml of methylene chloride each time
  2. washThe combined organic phases are washed with 50 ml of water and with 50 ml of saturated, aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8ce7733e94684fbd8ef0f0702a00127c
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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