Isopropylamine → 3-methyl-N-(1-methylethyl)-2-nitrobenzamide

HRID 475450Notes

Reaction equation

HRID 475450 reaction equation
[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.C(N(CC)CC)C.ClC(OCC)=O.[CH:27]([NH2:30])([CH3:29])[CH3:28]>C(Cl)Cl.O>[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:30][CH:27]([CH3:29])[CH3:28])=[O:7]

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 215753-Methyl-2-nitrobenzoic acid

Product 1

HCID 8902723-methyl-N-(1-methylethyl)-2-nitrobenzamideYield 80.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-methyl-2-nitrobenzoic acid (2.00 g, 11.0 mmol) and triethylamine (1.22 g, 12.1 mmol) in 25 mL of methylene chloride was cooled to 10° C. Ethyl chloroformate was carefully added and a solid precipitate formed. After stirring for 30 minutes isopropylamine (0.94 g, 16.0 mmol) was added and a homogeneous solution resulted. The reaction was stirred for an additional hour, poured into water and extracted with ethyl acetate. The organic extracts were washed with water, dried over magnesium sulfate and evaporated under reduced pressure to afford 1.96 g of the desired intermediate as a white solid melting at 126-128° C.

Workup

  1. customa solid precipitate formed
  2. additionwas added
  3. customa homogeneous solution resulted
  4. extractionextracted with ethyl acetate
  5. washThe organic extracts were washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7c82e4a810ce4671bac96a83a23a72e0
Source dataset
uspto-grants-2014_01
Patent number
US08637552B2

Reaction notes

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