4-Isopropylaniline → N-(4-isopropylphenyl)-8-nitrochroman-4-carboxamide

HRID 218552Notes

Reaction equation

HRID 218552 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][CH2:11][CH2:10][CH:9]2[C:14]([OH:16])=O)([O-:3])=[O:2].[CH:17]([C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)([CH3:19])[CH3:18].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[CH:17]([C:20]1[CH:26]=[CH:25][C:23]([NH:24][C:14]([CH:9]2[C:8]3[C:13](=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][CH:7]=3)[O:12][CH2:11][CH2:10]2)=[O:16])=[CH:22][CH:21]=1)([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 74644-IsopropylanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178541418-nitro-3,4-dihydro-2H-1-benzopyran-4-carboxylic acid

Product 1

HCID 17854307N-(4-isopropylphenyl)-8-nitrochroman-4-carboxamideYield 89.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-nitrochroman-4-carboxylic acid (3.0 g) and 4-isopropylaniline (2.0 g) in dimethylformamide (30 mL) were added N-hydroxybenzotriazole hydrate (2.0 g) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (2.8 g), and the mixture was stirred at room temperature. After the completion of the reaction, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give N-(4-isopropylphenyl)-8-nitrochroman-4-carboxamide (4.1 g).

Workup

  1. customAfter the completion of the reaction
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dfe9564918914edaac6cb49c840f9dfc
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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