Ammonia → Dimethyl 3-aminoglutaconate

HRID 342504Notes

Reaction equation

HRID 342504 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=O)=[O:4].C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH3:24].O>C1C=CC=CC=1.CCCCCC.CCOCC>[NH2:24][C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][C:3]([O:2][CH3:1])=[O:4]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 74591Dimethyl 3-oxoglutarate

Product 1

HCID 253819Dimethyl 3-aminoglutaconate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of dimethyl acetonedicarboxylate (44.1 ml, 0.3 mole) and p-toluene-sulfonic acid (0.19 g, 1 mmol) in benzene (50 ml) was bubbled NH3 gas for 30 min. The mixture was refluxed with azeotropic removal of water using Dean-Stark trap. The bubbling of NH3 gas and azeotropic removal of water was repeated three times to give a total 5 ml of water. The reaction mixture was diluted with benzene and filtered through celite. The filtrate was concentrated to give an amber oil, 50.75 g. An equal volume of ether was added to this oil and hexane added until cloudy, and stirred slowly overnight to afford a crystalline product. This crystalline was collected by filtration and washed once with 1/1 of ether/hexane to give 44.55 g (85.75%) of crystalline, mp 47°-50° C.

Workup

  1. customThe bubbling of NH3 gas and azeotropic removal of water
  2. customto give a total 5 ml of water
  3. filtrationfiltered through celite
  4. concentrationThe filtrate was concentrated
  5. customto give an amber oil, 50.75 g
  6. additionadded until cloudy
  7. customto afford a crystalline product
  8. filtrationThis crystalline was collected by filtration
  9. washwashed once with 1/1 of ether/hexane
  10. customto give 44.55 g (85.75%) of crystalline, mp 47°-50° C.

Sources & evidence

ORD record
ord-0f07ca910a3c439d9da20febc88a5e76
Source dataset
uspto-grants-1999_01
Patent number
US05859011

Reaction notes

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