Sodium Bicarbonate → HCID 178433699, compound

HRID 1634224Notes

Reaction equation

HRID 1634224 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:21]3[C:20](=[O:22])[NH:19][CH:18](O)[C:17](C)([CH3:24])[C:16]=3[CH:15]=[CH:14][C:13]=2[N:26]=1.[C:27]([O-])(O)=O.[Na+]>OS(O)(=O)=O>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:21]3[C:20](=[O:22])[NH:19][C:18]([CH3:27])=[C:17]([CH3:24])[C:16]=3[CH:15]=[CH:14][C:13]=2[N:26]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 178421872HCID 178421872, compound

Product 1

HCID 178433699HCID 178433699, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2-(2,6-Dichlorophenylamino)-6,6-dimethyl-7-hydroxy-7,8-dihydro-1H,6H-imidazo[4,5-h]isoquinoline-9-one (from Example 2) (45 mg, 0.11 mmol) was suspended in conc. H2SO4 (10 mL) and the resultant mixture was stirred at ambient temperature for 15 min. The solution was poured over ice, neutralized with NaHCO3 and filtered. The filtrate was triturated with water (10 mL) and centrifuged. The liquid was decanted, and the residual solid was triturated with methanol and centrifuged. The supernatant was decanted and the residue dried to give the title compound (35 mg, 84%). Mp>300° C.; MS (ES) 373 (MH+).

Workup

  1. additionThe solution was poured over ice
  2. filtrationfiltered
  3. customThe filtrate was triturated with water (10 mL)
  4. customThe liquid was decanted
  5. customthe residual solid was triturated with methanol
  6. customThe supernatant was decanted
  7. customthe residue dried

Sources & evidence

ORD record
ord-7b16b13d23cc4a638ca55f95849bfe0b
Source dataset
uspto-grants-2003_01
Patent number
US06506769B2

Reaction notes

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