Acetic Acid → 3-Chloro-1-phenylisoquinoline-4-carbaldehyde

HRID 443546Notes

Reaction equation

HRID 443546 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[N:13]=[C:14]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:15]2[C:20]([C:21]=1[C:22]#N)=[CH:19][CH:18]=[CH:17][CH:16]=2.C(O)(=[O:32])C.O>C1(C)C=CC=CC=1>[Cl:11][C:12]1[N:13]=[C:14]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:15]2[C:20]([C:21]=1[CH:22]=[O:32])=[CH:19][CH:18]=[CH:17][CH:16]=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14567253HCID 14567253, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 145672483-Chloro-1-phenylisoquinoline-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

In an atmosphere of argon and at -5° C. 10.7 ml of a 20% diisobutylaluminum hydride solution in toluene are slowly added dropwise to 2.64 g of 3-chloro-4-cyano-1-phenyl-isoquinoline in 150 ml of absolute toluene. The mixture is stirred for 10 minutes at 0° C. and then hydrolized with a small amount of glacial acetic acid until the reaction is weakly acid. Next, water is added and the toluene phase is separated. The organic phase is washed successively with saturated sodium bicarbonate solution and with water, dried and the solvent is removed under reduced pressure. The residue is rubbed with ether and recrystallized from ethyl acetate.

Workup

  1. customat -5° C
  2. customthe toluene phase is separated
  3. washThe organic phase is washed successively with saturated sodium bicarbonate solution and with water
  4. customdried
  5. customthe solvent is removed under reduced pressure
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-37eb4c15d3c345d0ab3b70f99e69a031
Source dataset
uspto-grants-1981_04
Patent number
US04260763

Reaction notes

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