Sodium Hydroxide → HCID 22623944, compound

HRID 567049Notes

Reaction equation

HRID 567049 reaction equation
C([NH:4][C:5]1[C:10]2[C:11](=[O:21])[N:12]([OH:20])[C:13](=[O:19])[C:14]3=[CH:15][CH:16]=[C:17]([Cl:18])[C:8]([C:9]=23)=[C:7]([N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:6]=1)(=O)C.[OH-].[Na+]>C(O)C>[NH2:4][C:5]1[C:10]2[C:11](=[O:21])[N:12]([OH:20])[C:13](=[O:19])[C:14]3=[CH:15][CH:16]=[C:17]([Cl:18])[C:8]([C:9]=23)=[C:7]([N:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)[CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22624003HCID 22624003, compound

Product 1

HCID 22623944HCID 22623944, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 4-acetylamino-7-chloro-2-hydroxy-6-(pyrrolidin-1yl)benzo[de]isoquinoline-1,3-dione (0.08 g, 0.2 mmol, from Example 138), 0.5N sodium hydroxide (5 mL) and ethanol (5 mL) was heated to solution and then stirred to room temperature over 1 hour. The ethanol was evaporated in vacuo, the aqueous diluted to 15 mL with water, and acidified with acetic acid. The mixture was extracted with dichloromethane, dried, filtered, and evaporated in vacuo. The residue was triturated with ether/petroleum ether to give 0.035 g of the title compound, mp 211-213° C.

Workup

  1. temperaturewas heated to solution
  2. customThe ethanol was evaporated in vacuo
  3. additionthe aqueous diluted to 15 mL with water
  4. extractionThe mixture was extracted with dichloromethane
  5. customdried
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was triturated with ether/petroleum ether

Sources & evidence

ORD record
ord-cafea5d0a9a24c66a74c888b3e9bb90d
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

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