Tert-Butylamine → HCID 10330217, compound

HRID 1017496Notes

Reaction equation

HRID 1017496 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][N:9]=1.[C:17]([NH2:21])([CH3:20])([CH3:19])[CH3:18].[OH-].[Na+]>C1(C)C=CC=CC=1.CN(C=O)C>[C:17]([NH:21][C:12](=[O:14])[C:11]1[CH:15]=[CH:16][C:8]([CH3:7])=[N:9][CH:10]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 1378606-Methylnicotinic acid

Product 1

HCID 10330217HCID 10330217, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
40 °C

Procedure

3.5 ml (40 mMol) Oxalylchloride and 57.4 μl (0.74 mMol) DMF were added to a suspension of 5.0 g (36.5 mMol) 6-methyl-nicotinic acid in 25 ml toluene and the system was heated to 40° C. for one hour. After diluting with 20 ml toluene and cooling to 0° C., 11.5 ml (109 mMol) tert.-butylamine were slowly added. After 30 minutes stirring at room temperature, 25 ml aqueous NaOH 2N were added and stirring pursued for 30 minutes. The phases were separated and the aqueous phase was extracted with toluene. The combined organic extracts were washed with water and brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (eluent:ethyl acetate/n-heptan 1:1) to yield 5.4 g (77%) N-tert.-butyl-6-methyl-nicotinamide as a light beige solid of m.p.=103.5-104.8° C.

Workup

  1. temperaturecooling to 0° C.
  2. stirringstirring
  3. waitpursued for 30 minutes
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with toluene
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (eluent:ethyl acetate/n-heptan 1:1)

Sources & evidence

ORD record
ord-beec11975cf04095b50075377aa81b72
Source dataset
uspto-grants-2002_11
Patent number
US06479483B2

Reaction notes

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