Dimethylamine → HCID 15617223, compound

HRID 2351610Notes

Reaction equation

HRID 2351610 reaction equation
[CH3:1][NH:2][CH3:3].C(O[C:7](=[O:19])[CH2:8][NH:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17])C.[O-][Si]([O-])=O.[Mg+2]>C(O)C.C(Cl)Cl>[CH3:1][N:2]([CH3:3])[C:7](=[O:19])[CH2:8][NH:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 61680MAGNESIUM SILICATE (synthetic)HCID 14390508HCID 14390508, compound

Product 1

HCID 15617223HCID 15617223, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Condensed dimethylamine (20 ml) was added in portions to a solution of crude N-(3-nitro-4-pyridinyl)glycine ethyl ester (4.0 g, 0.018 mole) in absolute ethanol (10 ml). The reaction was allowed to stir at ambient temperature over the weekend. The mixture was diluted with petroleum ether and the solid was collected by filtration. The solid 3-g was dissolved in tetrahydrofuran, filtered and diluted with isopropyl ether to produce a dark amorphous solid which was filtered off. The filtrate was further diluted with petroleum ether and placed in the freezer to produce a dark orange crystalline solid. The solid (2.5 g) was dissolved in methylene chloride, treated with Florisil.COPYRGT., and the filtrate was evaporated to a yellow solid, which was dried under high vacuum at 70° C. to give 1.8 g (45%), mp 142°-143° C.

Workup

  1. filtrationthe solid was collected by filtration
  2. dissolutionThe solid 3-g was dissolved in tetrahydrofuran
  3. filtrationfiltered
  4. additiondiluted with isopropyl ether
  5. customto produce a dark amorphous solid which
  6. filtrationwas filtered off
  7. additionThe filtrate was further diluted with petroleum ether
  8. customto produce a dark orange crystalline solid
  9. custom, and the filtrate was evaporated to a yellow solid, which
  10. customwas dried under high vacuum at 70° C.
  11. customto give 1.8 g (45%), mp 142°-143° C.

Sources & evidence

ORD record
ord-9aa0b88692d3406f8c1a1241a4d08820
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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