Water → N-{[1-(4-Fluorophenyl)-1,3-dihydro-2-benzofuran-5-yl]methylidene}hydroxylamine

HRID 382836Notes

Reaction equation

HRID 382836 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]=O)=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[NH2:27][OH:28].O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]=[N:27][OH:28])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 102204271-(4'-Fluorophenyl)-1,3-dihydroisobenzofuran-5-carbaldehyde

Product 1

HCID 71447165N-{[1-(4-Fluorophenyl)-1,3-dihydro-2-benzofuran-5-yl]methylidene}hydroxylamineYield 79.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
2.5 °C

Procedure

1-(4′-Fluorophenyl)-1,3-dihydroisobenzofuran-5-carbaldehyde (5.96 g) was dissolved in toluene (30 ml) and triethylamine (2.75 g) was flown in. Thereto was added hydroxylamine hydrochloride (1.88 g) and the mixture was reacted at 80-90° C. for 1 hr. Hot water (30 ml) was added to the reaction mixture and the mixture was partitioned while hot at 90° C. The organic layer was cooled to 0-5° C. and the resulting crystals were collected by filtration to give the title compound (5.02 g, yield:79.2%).

Workup

  1. customthe mixture was reacted at 80-90° C. for 1 hr
  2. customthe mixture was partitioned while hot at 90° C
  3. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-160bfb09c0964941bace886c981835e1
Source dataset
uspto-grants-2001_10
Patent number
US06310222B1

Reaction notes

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