4-Nitrobenzoic Acid → HCID 3419205, compound

HRID 715746Notes

Reaction equation

HRID 715746 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[CH3:31][CH:32]([CH3:36])[CH2:33][CH2:34][NH2:35].Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O>[CH2:34]([NH:35][C:8](=[O:10])[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=1)[CH2:33][CH:32]([CH3:36])[CH3:31]

Participants

8

Reactant 5

HCID 61084-Nitrobenzoic AcidHCID 7894IsoamylamineHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 3419205HCID 3419205, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Nitrobenzoic acid (0.8 g, 4.79 mmol) and 1-hydroxybenzotriazole hydrate (1.1 g, 7.18 mmol) in dimethylformamide (20 mL) was treated with N-methylmorpholine (1.8 mL, 16.75 mmol) and 3-methylbutan-1-amine (0.724 mL, 6.22 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.38 g, 7.18 mmol). The reaction mixture was stirred at room temperature for 17 hours. Water was added and the resulting suspension was stirred for 2 hours. The suspension was filtered and the solid collected was washed with water and dried to provide the title compound.

Workup

  1. stirringthe resulting suspension was stirred for 2 hours
  2. filtrationThe suspension was filtered
  3. customthe solid collected
  4. washwas washed with water
  5. customdried

Sources & evidence

ORD record
ord-459d2591f5d4489887b602d7fa8e9c33
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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