N,N-Dimethylaniline → HCID 178426134, compound

HRID 1685220Notes

Reaction equation

HRID 1685220 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6](O)[N:5]=[C:4]2[NH:9][N:10]=[C:11]([OH:12])[C:3]=12.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:6]1[N:5]=[C:4]2[NH:9][N:10]=[C:11]([OH:12])[C:3]2=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178429275HCID 178429275, compound

Product 1

HCID 178426134HCID 178426134, compound

Conditions

Temperature
115 °C

Procedure

2.5 g (15.14 mmol) of 4-methyl-1H-pyrazolo[3,4-b]pyridine-3,6-diol and 4.75 ml (39.2 mmol) of N,N-dimethylaniline were cautiously added to 60 ml of phosphorus oxychloride and the mixture was stirred at 115° C. for 5 h. The reaction mixture was concentrated and hydrolyzed with 30 g of ice. The product crystallized after some time. It was filtered off with suction and dried. Yield: 1.77 g (64%), M+H+: 184.1.

Workup

  1. concentrationThe reaction mixture was concentrated and hydrolyzed with 30 g of ice
  2. customThe product crystallized after some time
  3. filtrationIt was filtered off with suction
  4. customdried

Sources & evidence

ORD record
ord-4f197df1e45a498ea6bf79c458c09c0c
Source dataset
uspto-grants-2012_04
Patent number
US08148395B2

Reaction notes

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