Hydrochloric Acid → 5-Amino-7-(3-amino-3-methyl-1-pyrroldinyl)-1-cyclopropyl6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride

HRID 477028Notes

Reaction equation

HRID 477028 reaction equation
C([NH:4][C:5]1([CH3:37])[CH2:9][CH2:8][N:7]([C:10]2[C:19]([F:20])=[C:18]3[C:13]([C:14](=[O:29])[C:15]([C:24]([O:26]CC)=[O:25])=[CH:16][N:17]3[CH:21]3[CH2:23][CH2:22]3)=[C:12]([NH:30]C(OCC)=O)[C:11]=2[F:36])[CH2:6]1)(=O)C.[OH-].[Na+].[ClH:40]>C(O)C>[ClH:40].[NH2:30][C:12]1[C:11]([F:36])=[C:10]([N:7]2[CH2:8][CH2:9][C:5]([NH2:4])([CH3:37])[CH2:6]2)[C:19]([F:20])=[C:18]2[C:13]=1[C:14](=[O:29])[C:15]([C:24]([OH:26])=[O:25])=[CH:16][N:17]2[CH:21]1[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15729402Ethyl 7-(3-acetylamino-3-methyl-1-pyrrolidinyl)-1-cyclopropyl5-ethoxycarbonylamino-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 703958125-Amino-7-(3-amino-3-methyl-1-pyrroldinyl)-1-cyclopropyl6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 7-(3-acetylamino-3-methyl1-pyrroldinyl)-1-cyclopropyl-5-ethoxycarbonylamino-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate, 20% aqueous sodium hydroxide, and ethanol was refluxed for 12 hours. The reaction mixture was treated with activated carbon and adjusted at pH 1-2 with 10% hydrochloric acid. After cooling, the resulting crystals were collected by filtration and recrystallized from water-ethanol to give 5-amino-7-(3-amino-3-methyl-1-pyrroldinyl)-1-cyclopropyl6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride, m.p. 293°-297° C. (decomp.).

Workup

  1. temperaturewas refluxed for 12 hours
  2. additionThe reaction mixture was treated with activated carbon
  3. temperatureAfter cooling
  4. filtrationthe resulting crystals were collected by filtration
  5. customrecrystallized from water-ethanol

Sources & evidence

ORD record
ord-effb7b51a887407eb04b342b45d86366
Source dataset
uspto-grants-1989_12
Patent number
US04886810

Reaction notes

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