tert-Butoxy bis(dimethylamino)methane → HCID 58683693, compound

HRID 1991059Notes

Reaction equation

HRID 1991059 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[N:8]=[CH:7][CH:6]=[CH:5]2.C([O:19]C(N(C)C)N(C)C)(C)(C)C>CN(C=O)C>[N+:12]([C:11]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[N:8]2)=[CH:3][C:2]=1[CH:1]=[O:19])([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 58683734HCID 58683734, compound

Product 1

HCID 58683693HCID 58683693, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Methyl-7-nitroquinoline (Achylediani,R. et al. Izvestiya Akademii Nauk Gruzii, Seriya Khimicheskaya (1996), 22(1-4), 43-47) (14 g; 74 mmol) was dissolved in DMF (200 ml) and treated with tert.butoxy-bis(dimethylamino)methan (64.5 ml; 313 mmol) at 160° C. for 30 min. The reaction mixture was evaporated and purified by dissolving in THF (30 ml ), adding TBME (1.5 l) and filtering from the brown precipitate. The filtrate was evaporated to dryness and dissolved in THF (300 ml). NalO4 (95.6 g; 446 mmol) dissolved in water (5 l) was added under stirring within 45 min. The reaction mixture was extracted with EtOAc three times, the combined organic phases were dried over Na2SO4, evaporated to dryness and purified via chromatography (SiO2, toluene/TBME 96/10) to yield the title compound as yellowish crystals (9.5 g; 63%), which were used in the following step.

Workup

  1. customThe reaction mixture was evaporated
  2. custompurified
  3. dissolutionby dissolving in THF (30 ml )
  4. additionadding TBME (1.5 l)
  5. filtrationfiltering from the brown precipitate
  6. customThe filtrate was evaporated to dryness
  7. dissolutiondissolved in THF (300 ml)
  8. dissolutionNalO4 (95.6 g; 446 mmol) dissolved in water (5 l)
  9. additionwas added
  10. extractionThe reaction mixture was extracted with EtOAc three times
  11. dry with materialthe combined organic phases were dried over Na2SO4
  12. customevaporated to dryness
  13. custompurified via chromatography (SiO2, toluene/TBME 96/10)

Sources & evidence

ORD record
ord-f74b7d1eb06f4c14bdf8f241f192c551
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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