Methanol → 5-Nitro-N,N-dipropyl-isophthalamic acid

HRID 732563Notes

Reaction equation

HRID 732563 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[C:6]([C:7]([N:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.[OH-].[Li+].O.CO>C1COCC1>[N+:19]([C:17]1[CH:16]=[C:6]([C:7]([N:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=[C:4]([CH:18]=1)[C:3]([OH:22])=[O:2])([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 690570Methyl 3-[(dipropylamino)carbonyl]-5-nitrobenzoate

Product 1

HCID 688182175-Nitro-N,N-dipropyl-isophthalamic acidYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 5-nitro-N,N-dipropyl-isophthalamic acid methyl ester (1.000 g, 3.243 mmol) and lithium hydroxide (0.089 g, 3.730 mmol) in a mixture of THF (3.16 mL), water (1.58 mL) and methanol (1.58 mL). Stir the mixture at room temperature until the starting material is consumed. Concentrate and acidify with 1 N HCl. Extract with ethyl acetate, dry (magnesium sulfate) and concentrate to give the title compound (0.874 g, 92%).

Workup

  1. customis consumed
  2. concentrationConcentrate
  3. extractionExtract with ethyl acetate
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-e361356020ab4a4086265a0abb24b612
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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