Methanol → HCID 54482325, compound

HRID 1684611Notes

Reaction equation

HRID 1684611 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8](=O)[CH2:7][CH2:6]2.[N+:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O)([O-:16])=[O:15].N1CCCC1.C[OH:31]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][C:7](=[CH:20][C:19]1[CH:22]=[CH:23][CH:24]=[C:17]([N+:14]([O-:16])=[O:15])[CH:18]=1)[C:6]2=[O:31]

Participants

5

Reactant 4

HCID 887MethanolHCID 74493-NitrobenzaldehydeHCID 31268PyrrolidineHCID 2667436-METHOXYCHROMANONE

Product 1

HCID 54482325HCID 54482325, compoundYield 65%

Procedure

A mixture of 10.0 g (56.1 mmol) of 6-methoxychromanone, 8.48 g (56.1 mmol) of 3-nitrobenzaldehyde and 4.7 mL (56.1 mmol) of pyrrolidine in 30 mL methanol was allowed to stir at room temperature under N2 atmosphere. After 48 hours, the reaction mixture was filtered and the precipitate washed with methanol and dried to yield 11.44 g of yellow powder (65%). A small sample was recrystallized from isopropylether/CH2Cl2 for analytical data. M.p. 157°-159° C.; MS: C: 311.0794;F: 311.0796; 1H NMR (AC 300, CDCl3): δ5.27 (d, 2H, J=1.9 Hz); 3.84 (s, 3H); IR: 1670, 1490 cm-1. Analysis: calculated: C. 65.59, H 4.21, N 4.50%; found: C. 65.33, H4.57, N 4.47%.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe precipitate washed with methanol
  3. customdried

Sources & evidence

ORD record
ord-8c7a3c7d871b4211b882769201779a5d
Source dataset
uspto-grants-1997_06
Patent number
US05641789

Reaction notes

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