Sulfuric Acid → HCID 13246858, compound

HRID 1649872Notes

Reaction equation

HRID 1649872 reaction equation
[CH:1]([C:4]([CH3:18])([N:7]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:17])[C:5]#[N:6])([CH3:3])[CH3:2].S(=O)(=O)(O)[OH:20]>>[CH:1]([C:4]([CH3:18])([N:7]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:17])[C:5]([NH2:6])=[O:20])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 13246848HCID 13246848, compound

Product 1

HCID 13246858HCID 13246858, compound

Conditions

Temperature
0 °C

Procedure

To 330 mL concentrated sulfuric acid is added portion wise with thorough stirring 298 g of finely divided 5,7-dihydro-alpha-isopropyl-alpha-methyl-5,7-dioxo-6H-pyrrolo[3,4-b]pyridine-6-acetonitrile so that the temperature did not go about 72° C. After the addition the temperature is adjusted to 60°-65° C. and maintained there for 11/2 hours. The mixture is cooled, quenched with ice and finally diluted to approximately 4 liters. After adding 454 g sodium acetate and cooling at 0° C. for 2 hours the mixture is filtered, the solids collected and washed twice with 500 mL water containing sodium acetate followed by water to remove all the sulfuric acid. The solid is dried to give 289 g of product, mp 176°-178° C. Material made in a similar way and analytically pure had mp 188°-190° C.

Workup

  1. customdid not go about 72° C
  2. additionAfter the addition the temperature
  3. customis adjusted to 60°-65° C.
  4. temperaturemaintained there for 11/2 hours
  5. temperatureThe mixture is cooled
  6. customquenched with ice
  7. additionfinally diluted to approximately 4 liters
  8. additionAfter adding 454 g sodium acetate
  9. filtrationis filtered
  10. customthe solids collected
  11. washwashed twice with 500 mL water
  12. additioncontaining sodium acetate
  13. customto remove all the sulfuric acid
  14. customThe solid is dried

Sources & evidence

ORD record
ord-dff83713c7624e11aa8d226fd855871c
Source dataset
uspto-grants-1990_05
Patent number
US04921961

Reaction notes

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