hydroxylamine-O-sulfonic acid → HCID 13669915, compound

HRID 256316Notes

Reaction equation

HRID 256316 reaction equation
[CH2:1]([C:3]1[C:4]([O:15][CH3:16])=[N:5][C:6]2[N:7]([CH:10]=[C:11]([CH:13]=O)[N:12]=2)[C:8]=1[CH3:9])[CH3:2].[NH2:17]OS(O)(=O)=O>O>[CH2:1]([C:3]1[C:4]([O:15][CH3:16])=[N:5][C:6]2[N:7]([CH:10]=[C:11]([C:13]#[N:17])[N:12]=2)[C:8]=1[CH3:9])[CH3:2]

Participants

4

Reactant 2

HCID 76284hydroxylamine-O-sulfonic acidHCID 13304948HCID 13304948, compound

Product 1

HCID 13669915HCID 13669915, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a rapidly stirred suspension of 19.84 g of 6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidine-2-carboxaldehyde in 300 ml of water at room temperature was added all at once a solution of 13.30 g of hydroxylamine-o-sulfonic acid in 250 ml of water. After 40 minutes when the intermediate had precipitated, 8 g of solid sodium hydroxide were added and the intermediate dissolved. After 1 hour when the product had precipitated, the mixture was filtered and the solid was washed with water, dried, then crystallized from ethyl acetate to obtain 16.18 g of 6-ethyl-7-methoxy-5-methylimidazo [1,2-a]pyrimidine-2-carbonitrile (83% yield) as a pale yellow solid melting at 166°-168° C.

Workup

  1. customAfter 40 minutes when the intermediate had precipitated
  2. addition8 g of solid sodium hydroxide were added
  3. dissolutionthe intermediate dissolved
  4. customAfter 1 hour when the product had precipitated
  5. filtrationthe mixture was filtered
  6. washthe solid was washed with water
  7. customdried
  8. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-61c774323e444bc5bf8cd0183172ac0a
Source dataset
uspto-grants-1987_10
Patent number
US04703049

Reaction notes

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