Sodium Bicarbonate → HCID 178433699, compound

HRID 1835090Notes

Reaction equation

HRID 1835090 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 (1 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-b37baaf2f4d444928f44a3af62118e9b
Source dataset
uspto-grants-2004_08
Patent number
US06770639B2

Reaction notes

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