2-Nitrobenzaldehyde → HCID 20192976, compound

HRID 328576Notes

Reaction equation

HRID 328576 reaction equation
[CH3:1][O:2][C:3](=[O:8])/[C:4](/N)=[CH:5]/[CH3:6].[CH3:9][S:10]([CH2:13][C:14](=O)[CH3:15])(=[O:12])=[O:11].[N+:17]([C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O)([O-:19])=[O:18].C[N:29](C)P(=O)(N(C)C)N(C)C>C(OCC)(=O)C>[CH3:6][C:5]1[NH:29][C:14]([CH3:15])=[C:13]([S:10]([CH3:9])(=[O:12])=[O:11])[CH:22]([C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[N+:17]([O-:19])=[O:18])[C:4]=1[C:3]([O:2][CH3:1])=[O:8]

Participants

6

Reactant 4

HCID 111012-NitrobenzaldehydeHCID 12679HexamethylphosphoramideHCID 786951-(Methylsulphonyl)acetoneHCID 12743422HCID 12743422, compound

Product 1

HCID 20192976HCID 20192976, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

23.0 g of aminocrotonic acid methyl ester and 40.8 g of methylsulphonylacetone are added to 30.2 g of o-nitrobenzaldehyde dissolved in 200 ml of hexamethylphosphoric acid triamide. The mixture is then stirred for 3 hours at a bath temperature of 90°-100° C. The mixture is cooled and dissolved in 1,000 ml of ethyl acetate and the solution is washed with 400 ml of half-saturated sodium chloride solution, with twice 200 ml of 2 N sodium carbonate solution and with twice 500 ml of water. The ethyl acetate solution is dried with sodium carbonate and evaporated. Crystallisation of the residue from ethyl acetate/ether gives 2,6-dimethyl-3-carbomethoxy-5-methylsulphonyl- 4-(2-nitrophenyl)- 1,4-dihydropyridine of melting point 211°-212° C.

Workup

  1. temperatureThe mixture is cooled
  2. washthe solution is washed with 400 ml of half-saturated sodium chloride solution, with twice 200 ml of 2 N sodium carbonate solution and with twice 500 ml of water
  3. dry with materialThe ethyl acetate solution is dried with sodium carbonate
  4. customevaporated
  5. customCrystallisation of the residue from ethyl acetate/ether

Sources & evidence

ORD record
ord-d897f2a396314f5682aab216316d5e7c
Source dataset
uspto-grants-1977_04
Patent number
US04017629

Reaction notes

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