2-Aminophenol → HCID 70431425, compound

HRID 652953Notes

Reaction equation

HRID 652953 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][C:23]([OH:25])=O)[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20].[I-].ClC1C=CC=C[N+]=1C.C(N(CC)CC)C.[NH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[OH:49]>C(#N)C.O>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][C:23]([NH:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[OH:49])=[O:25])[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20]

Participants

7

Reactant 4

HCID 58012-AminophenolHCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 53972623HCID 53972623, compound

Product 1

HCID 70431425HCID 70431425, compoundYield 12.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 1.21 g (3.40 mmol) of 3-{3,4-di-(β-methoxyethoxymethoxy)phenyl}-2-propenic acid in dry acetonitrile (30 ml) were added in an argon atmosphere 1.73 g (6.76 mmol) of 2-chloro-1-methylpyridinium iodide and 2.40 ml (17.2 mmol) of triethylamine and 799 mg (7.32 mmol) of o-aminophenol, successively. The mixture was reacted at room temperature for 60 hours, followed by addition of water. The mixture was extracted with ethyl acetate, and the organic layer was successively washed with 1N-aqueous hydrochloric acid, water, aqueous solution of sodium carbonate and water. The organic layer was concentrated under reduced pressure, and the residue thus obtained was subjected to silica gel column chromatography. There was obtained 188 mg (0.420 mmol) of N-[3-{3,4-di(β-methoxyethoxymethoxy)phenyl}-2-propenoyl]-o-aminophenol.

Workup

  1. customThe mixture was reacted at room temperature for 60 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was successively washed with 1N-aqueous hydrochloric acid, water, aqueous solution of sodium carbonate and water
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe residue thus obtained

Sources & evidence

ORD record
ord-114eb47e913146beb53eee323bf2caaf
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

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