Hydrochloric Acid → HCID 178524377, compound

HRID 1591639Notes

Reaction equation

HRID 1591639 reaction equation
[NH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])[NH2:2].C([O:14][C:15]([C:17]1[CH:18]=[N:19][C:20]2[C:25]([C:26]=1Cl)=[CH:24][CH:23]=[CH:22][C:21]=2[F:28])=O)C.[OH-].[Li+].Cl>C(O)CCC.O.O1CCCC1>[F:28][C:21]1[C:20]2[NH:19][CH:18]=[C:17]3[C:15](=[O:14])[N:1]([C:3]4[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=4)[C:6]([OH:8])=[O:7])[N:2]=[C:26]3[C:25]=2[CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 1479093ethyl 4-chloro-8-fluoroquinoline-3-carboxylateHCID 27365213-Hydrazinobenzoic acid

Product 1

HCID 178524377HCID 178524377, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

3-Hydrazinobenzoic acid (1.91 g, 0.013 mol) was added in one portion to a stirred solution of 4-chloro-8-fluoro-quinoline-3-carboxylic acid ethyl ester (2.93 g, 0.011 mol) in n-butanol (60 ml) at room temperature. The solution was heated to reflux for 16 h, cooled to room temperature and the resulting yellow solid filtered, washed with tert-butyl methyl ether and then dried. The solid was redissolved in a solution of tetrahydrofuran water (2:1; 21 ml) and lithium hydroxide (1.27 g, 0.031 mol) was then added. After stirring at room temperature for 16 h, concentrated hydrochloric acid (3 ml) was added dropwise to the mixture to precipitate a yellow solid which was filtered and dried under vacuum to give the title compound (intermediate 3) (2.32 g, 63%) as a bright yellow solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 16 h
  3. filtrationthe resulting yellow solid filtered
  4. washwashed with tert-butyl methyl ether
  5. customdried
  6. additionwas then added
  7. customto precipitate a yellow solid which
  8. filtrationwas filtered
  9. customdried under vacuum

Sources & evidence

ORD record
ord-4080cdf564164c398bb5043b86c41add
Source dataset
uspto-grants-2007_11
Patent number
US07291612B2

Reaction notes

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