Hydrochloric Acid → HCID 54389688, compound

HRID 128701Notes

Reaction equation

HRID 128701 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]([CH:18]([CH2:25][CH2:26][NH:27][CH3:28])[CH2:19][CH2:20]CC(O)=O)[N:8]=2)=[CH:4][CH:3]=1.[OH-:31].[Na+].Cl.C([O:36][CH2:37]C)C>CO>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]([CH:18]([CH2:25][CH2:26][NH:27][CH3:28])[CH2:19][CH2:20][C:37]([OH:36])=[O:31])[N:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 54284703HCID 54284703, compound

Product 1

HCID 54389688HCID 54389688, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

15 g 4-(4-chlorobenzyl)-2-(5-methylamino-1-carboxymethyl-3-pentyl)1(2H)-phthalazinone (Example 2) are dissolved in 150 ml methanol and reacted with 21 ml 5M sodium hydroxide solution. The solution is heated for 1.5 hours to 50° C., then concentrated in a rotary evaporator, and the residue reacted is with 105 ml 1M HCl (pH 6). The aqueous solution is first shaken with diethylether to remove nonpolar impurities and then extracted with dichloromethane. The combined dichloromethane phases are concentrated, and the raw product is crystallized from ethanol. The crystalline product is precipitated absorptively with ether and dried in a vacuum (55° C./2 Torr).

Workup

  1. temperatureThe solution is heated for 1.5 hours to 50° C.
  2. concentrationconcentrated in a rotary evaporator
  3. customthe residue reacted
  4. customto remove nonpolar impurities
  5. extractionextracted with dichloromethane
  6. concentrationThe combined dichloromethane phases are concentrated
  7. customthe raw product is crystallized from ethanol
  8. customThe crystalline product is precipitated absorptively with ether
  9. customdried in a vacuum (55° C./2 Torr)

Sources & evidence

ORD record
ord-1649732b9728455384b860dc94329dad
Source dataset
uspto-grants-1995_11
Patent number
US05464838

Reaction notes

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