Hydrochloric Acid → HCID 10494238, compound

HRID 247040Notes

Reaction equation

HRID 247040 reaction equation
[NH2:1][C:2]1[C:7]2[C:8](=[O:14])[N:9]([CH2:11][CH2:12][CH3:13])[CH2:10][C:6]=2[N:5]=[C:4]2[N:15]([CH:18]=[CH2:19])[N:16]=[CH:17][C:3]=12.Cl.[C:21](=O)([O-])[O-].[Na+].[Na+].[C:27](#N)[CH3:28]>>[NH2:1][C:2]1[C:7]2[C:8](=[O:14])[N:9]([CH2:11][CH2:12][CH3:13])[CH2:10][C:6]=2[N:5]=[C:4]2[N:15]([CH2:18][CH2:19][C:21]#[C:27][CH3:28])[N:16]=[CH:17][C:3]=12

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 20161348HCID 20161348, compound

Product 1

HCID 10494238HCID 10494238, compound

Procedure

A mixture of 4-amino-6,7-dihydro-6-(n-propyl)-1-vinylpyrazolo[3,4-b]pyrrolo[3,4-e]pyridin5-(1H)-one (9.9 g.) and acetonitrile (250 ml.) was stirred while 6N aqueous hydrochloric acid (100 ml.) was added. The mixture was heated under reflux for 3.5 hours under nitrogen. The cooled suspension was neutralized by the cautious addition of saturated aqueous sodium carbonate and the acetonitrile was removed at reduced pressure. The aqueous suspension of product was chilled to 4° overnight. The precipitated white solid was collected by filtration, washed with water, and dried in vacuo. There was thus obtained 8.0 g. of 4-amino-6,7-dihydro-1H-6-n-propylpyrazolo[3,4-b]pyrrolo[3,4-e]pyridin-5-(1H)-one. Recrystallization from acetonitrile gave a sample: m.p. 278°-281 °.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 3.5 hours under nitrogen
  4. customthe acetonitrile was removed at reduced pressure
  5. additionThe aqueous suspension of product
  6. temperaturewas chilled to 4° overnight
  7. filtrationThe precipitated white solid was collected by filtration
  8. washwashed with water
  9. customdried in vacuo
  10. customRecrystallization from acetonitrile
  11. customgave a sample

Sources & evidence

ORD record
ord-8653de972a4f49bba1c41f634737e641
Source dataset
uspto-grants-1987_11
Patent number
US04705793

Reaction notes

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