tert-Butoxy bis(dimethylamino)methane → HCID 58683726, compound

HRID 1991063Notes

Reaction equation

HRID 1991063 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C([O:19]C(N(C)C)N(C)C)(C)(C)C>CN(C=O)C>[N+:12]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[CH:1]=[O:19])[N:9]=[CH:8][CH:7]=[CH:6]2)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 3640834HCID 3640834, compound

Product 1

HCID 58683726HCID 58683726, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Methyl-6-nitroquinolin (1.22 g; 6.5 mmol) and tert.butoxy-bis(dimethylamino)methan (5.2 ml; 27.3 mmol) in DMF (13 ml) were heated for 15 min. in an oil bath, which was preheated to 160° C. The reaction mixture was evaporated to dryness, taken up in THF (26 ml). NalO4 (8.3 g; 39 mmol) in water (520 ml) was added at room. temperature within 1.5 h and after stirring for another 1 h the reaction mixture was extracted with EtOAc twice. The combined organic phases were dried over Na2SO4, evaporated and purified via chromatography (SiO2; TBME) to yield the title compound as a yellow foam (920 mg; 70%).

Workup

  1. customwas preheated to 160° C
  2. customThe reaction mixture was evaporated to dryness
  3. additionNalO4 (8.3 g; 39 mmol) in water (520 ml) was added at room
  4. extractionwas extracted with EtOAc twice
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. customevaporated
  7. custompurified via chromatography (SiO2; TBME)

Sources & evidence

ORD record
ord-f2ae88e8a1f94ba6890f2b50711194c6
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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