Sodium Hydroxide → HCID 12624922, compound

HRID 2050333Notes

Reaction equation

HRID 2050333 reaction equation
[Cl-:1].[Al+3].[Cl-].[Cl-].CO[CH:7](OC)[CH:8]([N:10]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=1)[C:11](=[O:13])[CH3:12])Cl.[OH-].[Na+]>ClCCCl>[C:11]([N:10]1[CH:8]=[CH:7][C:20]2[C:15](=[C:16]([Cl:1])[C:17]([Cl:21])=[CH:18][CH:19]=2)[CH2:14]1)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 70587928HCID 70587928, compound

Product 1

HCID 12624922HCID 12624922, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 91 g. (0.682 m.) of aluminum chloride in 1400 ml. of 1,2-dichloroethane was added a solution of N-acetyl-2,3-dichlorobenzylaminoacetaldehyde dimethyl acetal (45.5 g., 0.149 m.) in 230 ml. of 1,2-dichloroethane over an hour, the temperature staying below 30° C. The mixture was then cooled to 0° C. and 1000 ml. of 40% NaOH was added. The mixture was stirred and the layers separated. The aqueous fraction was extracted with 500 ml. of 1,2-dichloroethane and the combined organic layers were washed with 300 ml. of water and dried over magnesium sulfate. Evaporation and trituration with ether gave 2-acetyl-7,8-dichloro-1,2-dihydroisoquinoline.

Workup

  1. additionTo a suspension of 91 g
  2. customstaying below 30° C
  3. customthe layers separated
  4. extractionThe aqueous fraction was extracted with 500 ml
  5. washof 1,2-dichloroethane and the combined organic layers were washed with 300 ml
  6. dry with materialof water and dried over magnesium sulfate
  7. customEvaporation and trituration with ether

Sources & evidence

ORD record
ord-eb35221687cc414188f5456b2d1beafc
Source dataset
uspto-grants-1980_04
Patent number
US04200754

Reaction notes

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