Sodium Hydroxide → HCID 23146285, compound

HRID 2077368Notes

Reaction equation

HRID 2077368 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[CH:15][C:9]=1[C:10]([N:12]([CH3:14])[CH3:13])=O.[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[CH3:14][N:12]([CH2:10][C:9]1[CH:15]=[CH:16][CH:17]=[C:18]([NH2:19])[C:8]=1[NH2:7])[CH3:13]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 587361062-Amino-N,N-dimethyl-3-nitrobenzamide

Product 1

HCID 23146285HCID 23146285, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

1M Lithium aluminium hydride in THF (18.1 ml, 18.1 mmol) was added dropwise over 5 min. to a stirred, ice cooled solution of 2-Amino-N,N-dimethyl-3-nitro-benzamide, D14 (1.26 g, 6.03 mmol) in anhydrous THF (40 ml) under argon. The reaction mixture was stirred at 0° C. for 0.5 h then at room temperature for a further 2 h before being recooled in ice, as water (3.2 ml), 2N sodium hydroxide (3.6 ml) and water (3.2 ml) were added dropwise sequentially. The mixture was stirred for 10 min, solid Na2SO4 added and stirring continued for 10 min. Solids were filtered, washed with ethyl acetate and the combined organics evaporated in vacuo to give the title compound as an orange solid (0.9 g, 91%).

Workup

  1. additionwere added dropwise sequentially
  2. stirringThe mixture was stirred for 10 min
  3. stirringstirring
  4. waitcontinued for 10 min
  5. filtrationSolids were filtered
  6. washwashed with ethyl acetate
  7. customthe combined organics evaporated in vacuo

Sources & evidence

ORD record
ord-3ffbbc1030114d6db22de90a79e91c29
Source dataset
uspto-grants-2011_04
Patent number
US07928125B2

Reaction notes

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