Chloroacetaldehyde → HCID 178510512, compound

HRID 1627020Notes

Reaction equation

HRID 1627020 reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[C:6]([O:10]C)[C:3]=1[C:4]#[N:5].Cl[CH2:13][CH:14]=O.CCOCC>CCO>[OH:10][C:6]1[CH:7]=[CH:8][N:9]2[CH:13]=[CH:14][N:1]=[C:2]2[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 3283Diethyl EtherHCID 27353592-Amino-4-Methoxynicotinonitrile

Product 1

HCID 178510512HCID 178510512, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of compound D3 (2 g, 13.404 mmol) in EtOH (5 ml) was added chloroacetaldehyde (1.58 g, 20.11 mmol). The reaction mixture was subjected to microwave heating at 150° C. for 45 min. After cooling to room temperature, the solvent was evaporated in vacuo. The residue thus obtained was then treated with Et2O and a solid precipitated. The solid thus obtained was filtered off, washed with EtOAc and dried in vacuo to yield compound D21 (1.5 g, 70%).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was evaporated in vacuo
  3. customThe residue thus obtained
  4. customa solid precipitated
  5. customThe solid thus obtained
  6. filtrationwas filtered off
  7. washwashed with EtOAc
  8. customdried in vacuo
  9. customto yield compound D21 (1.5 g, 70%)

Sources & evidence

ORD record
ord-dc0a0e7dd45746a79c35e7101697fbd2
Source dataset
uspto-grants-2014_07
Patent number
US08785486B2

Reaction notes

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