3-Nitrobenzoic acid → HCID 80107846, compound

HRID 1487124Notes

Reaction equation

HRID 1487124 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].[O:13]1[CH2:16][CH:15]([NH2:17])[CH2:14]1.CCN=C=NCCCN(C)C.Cl>N1C=CC=CC=1.O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH:17][CH:15]1[CH2:16][O:13][CH2:14]1)=[O:9])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 84973-Nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 98339233-Oxetanamine

Product 1

HCID 80107846HCID 80107846, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

3-Nitrobenzoic acid (0.50 g, 2.99 mmol), oxetan-3-amine (0.219 g, 2.99 mmol) were taken in pyridine (0.5 ml) and under nitrogen atmosphere and EDC.HCl (0.574 g, 2.99 mmol) was added. The reaction mixture was stirred at room temperature for 10 hrs. After completion of reaction, the reaction mixture was diluted with water (5 ml) and extracted with ethyl acetate (2×5 ml). Combined organic layer was dried over sodium sulfate and concentrated under vacuum to afford the title compound (600 mg).

Workup

  1. customAfter completion of reaction
  2. extractionextracted with ethyl acetate (2×5 ml)
  3. dry with materialCombined organic layer was dried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-21add6f2c7e64038abe94497f9ea60da
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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