Acetaldehyde → HCID 86683221, compound

HRID 1852150Notes

Reaction equation

HRID 1852150 reaction equation
C[CH2:2][N:3]([CH:7]([CH3:9])C)[CH:4]([CH3:6])C.[Cl:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)C=C(NC)[N:12]=1.C(=O)C.C([BH3-])#N>CO.C(O)(=O)C>[Cl:10][C:11]1[C:20]2[C:19](=[CH:18][C:17]([O:21][CH3:22])=[CH:16][CH:15]=2)[CH:9]=[C:7]([N:3]([CH2:4][CH3:6])[CH3:2])[N:12]=1

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 81531DiisopropylethylamineHCID 498716Cyano-borohydrideHCID 86683222HCID 86683222, compound

Product 1

HCID 86683221HCID 86683221, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Hunig's base (0.235 mL, 1.347 mmol) was added to a solution of 1-chloro-6-methoxy-N-methylisoquinolin-3-amine (150 mg, 0.674 mmol) and acetaldehyde (0.042 mL, 0.741 mmol) in MeOH (5 mL) and stirred for 30 min Acetic Acid (1 mL) and Cyanoborohydride, polymer supported (2 mmol/gram) (50 mg, 0.674 mmol) were then added and the reaction stirred at r.t. for 2 hrs. Reaction filtered through nylon frit filter and evaporated on rotovap to give the crude product with no purification. The material was taken up in EtOAc and washed with sat. sodium bicarbonate. The organic layer was collected, dried over MgSO4, filtered and evaporated to give the expected product 1-chloro-N-ethyl-6-methoxy-N-methylisoquinolin-3-amine (140 mg, 83% yield) as a dark orange solid. MS: MS m/z 251.15(M++1).

Workup

  1. additionwere then added
  2. customReaction
  3. filtrationfiltered through nylon frit
  4. filtrationfilter
  5. customevaporated on rotovap
  6. customto give the crude product
  7. customwith no purification
  8. washwashed with sat. sodium bicarbonate
  9. customThe organic layer was collected
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-f186083d77ff413c9da888f3a7978926
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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