4-Dimethylamino-1-naphthaldehyde → MAZ51

HRID 2190104Notes

Reaction equation

HRID 2190104 reaction equation
[N:1]1[C:2](=[O:10])[CH:3]=[C:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[CH:5]2.[CH3:11][N:12]([CH3:25])[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH:23]=O)=[CH:15][CH:14]=1>N1CCCCC1.C(O)C>[CH3:11][N:12]([CH3:25])[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH:23]=[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:10])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 6080524-Dimethylamino-1-naphthaldehydeHCID 17904787Indol-2-one

Product 1

HCID 24906291MAZ51

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1.33 g of indole-2-one (10 mmol), 1.99 g of 4-dimethylamino-1-naphthaldehyde (10 mmol) and 3 drops of piperidine are refluxed in 40 ml of ethanol for 5 hours. The desired product precipitates as an orange solid during the reaction. After cooling to room temperature, the product is filtered off, washed with ethanol and dried in vacuo. Yield 2.67 g (85%).

Workup

  1. customThe desired product precipitates as an orange solid during the reaction
  2. filtrationthe product is filtered off
  3. washwashed with ethanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-521069500cef401a84810a2c0dfce2b0
Source dataset
uspto-grants-2012_12
Patent number
US08324267B2

Reaction notes

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