Hydroxyamine hydrochloride → HCID 178471466, compound

HRID 2189796Notes

Reaction equation

HRID 2189796 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[N:6][N:7]2[CH2:12][C:13]([CH3:20])([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:2].Cl.[NH2:22][OH:23].C([O-])(O)=O.[Na+]>CO>[OH:23][NH:22][C:1](=[NH:2])[C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[N:6][N:7]2[CH2:12][C:13]([CH3:20])([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 59316699Ethyl 3-(4-cyano-1H-indazol-1-yl)-2,2-dimethylpropanoate

Product 1

HCID 178471466HCID 178471466, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 3-(4-cyano-1H-indazol-1-yl)-2,2-dimethylpropanoate (D102) (348 mg, 1.28 mmol), hydroxylamine hydrochloride (1.087 g, 10.26 mmol), NaHCO3 (1.078 g, 12.83 mmol) in MeOH (20 ml) was heated at 65° C. for 24 h then at room temperature over the weekend. The mixture was filtered, concentrated, treated with water and vigorously stirred for 10 mins, filtered and dried to give a colourless solid, dried overnight in vacuo at 45° C. to give the title compound (373 mg, 90%). MS (ES) C15H20N4O3 requires 304, found 305 [M+H]+

Workup

  1. customat room temperature
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. additiontreated with water
  5. filtrationfiltered
  6. customdried
  7. customto give a colourless solid
  8. customdried overnight in vacuo at 45° C.

Sources & evidence

ORD record
ord-c5487efb761449acae7c40bc07a0e1e3
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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