Sodium Hydroxide → HCID 15085983, compound

HRID 1073286Notes

Reaction equation

HRID 1073286 reaction equation
C[O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[N:8]=[C:7]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[CH:18][CH:17]=2)[C:6]=1[NH2:28])=[O:4].[OH-].[Na+]>C(O)C>[NH2:28][C:6]1[C:7]([C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[CH:20][CH:21]=2)=[N:8][C:9]2[C:14]([C:5]=1[C:3]([OH:4])=[O:2])=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15085984HCID 15085984, compound

Product 1

HCID 15085983HCID 15085983, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 0.097 g of 3-amino-6-fluoro-2-[4-(3-pyridinyl)-phenyl]-4-quinolinecarboxylic acid methyl ester in 10 ml of ethanol was added 1.0 ml of 2.5N aqueous sodium hydroxide. The solution was stirred at reflux for 0.5 hour. The solution was concentrated to a small volume in vacuo and then diluted with 10 ml of water. The solution was acidified with 0.2 ml of glacial acetic acid, warmed briefly and cooled to 20° C. The solid was collected, washed with water, and dried in vacuo, giving 0.076 g of the desired compound as a yellow powder, mp 260°-268° C.

Workup

  1. temperatureat reflux for 0.5 hour
  2. concentrationThe solution was concentrated to a small volume in vacuo
  3. additiondiluted with 10 ml of water
  4. temperaturewarmed briefly
  5. customThe solid was collected
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-fe9851b34cc34fd2a60961eea6689f52
Source dataset
uspto-grants-1990_11
Patent number
US04968702

Reaction notes

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