3-Nitrobenzoic acid → HCID 89815442, compound

HRID 1487126Notes

Reaction equation

HRID 1487126 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([NH2:6])[CH2:2]1.[N+:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](O)=[O:14])([O-:9])=[O:8].CCN=C=NCCCN(C)C.Cl>N1C=CC=CC=1.O>[N+:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([NH:6][CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)=[O:14])([O-:9])=[O:8]

Participants

6

Reactant 3

HCID 84973-Nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3365553Oxolan-3-amine

Product 1

HCID 89815442HCID 89815442, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Tetrahydrofuran-3-amine (0.1 g, 1.148 mmol) and 3-nitrobenzoic acid (0.192 g, 1.148 mmol) were taken in pyridine (2 ml), to the mixture EDC.HCl (0.220 g, 1.148 mmol) was added, the reaction mixture was stirred under nitrogen for 10 hrs at room temperature. The reaction mixture was diluted with cold water (15 ml), extracted with ethyl acetate (2×10 ml). Combined organic layer was washed with satd. aq. sod bicarbonate and dil HCl, the organic layer was dried over sodium sulfate and concentrated under vacuum to afford the title product (240 mg).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate (2×10 ml)
  3. washCombined organic layer was washed with satd
  4. dry with materialaq. sod bicarbonate and dil HCl, the organic layer was dried over sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-97c29d20f0ec488894729de74eb93dcc
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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