2-Nitrobenzaldehyde → HCID 21442894, compound

HRID 328578Notes

Reaction equation

HRID 328578 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[NH2:12]/[C:13](/[CH3:23])=[CH:14]\[C:15]([N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16].[CH3:24][S:25]([CH2:28][C:29](=O)[CH3:30])(=[O:27])=[O:26]>CN(C)P(=O)(N(C)C)N(C)C.C(OCC)(=O)C>[CH3:23][C:13]1[NH:12][C:29]([CH3:30])=[C:28]([S:25]([CH3:24])(=[O:27])=[O:26])[CH:6]([C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N+:1]([O-:3])=[O:2])[C:14]=1[C:15]([N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16]

Participants

6

Reactant 3

HCID 111012-NitrobenzaldehydeHCID 786951-(Methylsulphonyl)acetoneHCID 768586HCID 768586, compound

Product 1

HCID 21442894HCID 21442894, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

15.1 g of o-nitrobenzaldehyde, 16.8 g of 3-aminocrotonic acid piperidide and 13.6 g of methylsulphonylacetone are stirred in 100 ml of hexamethylphosphoric acid triamide for 10 hours under nitrogen at a bath temperature of 115° C. The mixture is cooled and dissolved in 600 ml of ethyl acetate and the solution is washed with a mixture of 600 ml of water, 90 ml of methanol and 90 ml of sodium chloride solution. The organic phase is separated off and the aqueous phase, in which a dark brown product precipitates, is filtered. The crystalline product is dried by azeotropic distillation on a rotary evaporator and treated twice in methanol/chloroform with animal charcoal. The filtrate is evaporated and the residue is recrystallised from isopropanol. 2,6-Dimethyl- 3-piperidinocarbonyl-4-(2-nitrophenyl)-5-methylsulphonyl-1,4-dihydropyridine, which is thus obtained, melts at 275°-276° C.

Workup

  1. temperatureThe mixture is cooled
  2. washthe solution is washed with a mixture of 600 ml of water, 90 ml of methanol and 90 ml of sodium chloride solution
  3. customThe organic phase is separated off
  4. customthe aqueous phase, in which a dark brown product precipitates
  5. filtrationis filtered
  6. customThe crystalline product is dried by azeotropic distillation on a rotary evaporator
  7. additiontreated twice in methanol/chloroform with animal charcoal
  8. customThe filtrate is evaporated
  9. customthe residue is recrystallised from isopropanol

Sources & evidence

ORD record
ord-084784aa2f614ee9881e2c8708a91a54
Source dataset
uspto-grants-1977_04
Patent number
US04017629

Reaction notes

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