Triethylamine → HCID 18381684, compound

HRID 2268927Notes

Reaction equation

HRID 2268927 reaction equation
[Br-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH:9]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)O[C:7]2=[O:32].[N:33]1[CH:38]=[CH:37][C:36]([CH:39]=O)=[CH:35][CH:34]=1.C(N(CC)CC)C.O.[NH2:49][NH2:50]>C(Cl)Cl.O>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10]([C:9]([CH2:39][C:36]3[CH:37]=[CH:38][N:33]=[CH:34][CH:35]=3)=[N:49][NH:50][C:7]2=[O:32])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 133894-PyridinecarboxaldehydeHCID 24654Hydrazine hydrate (1:1)HCID 11562468(5-Methoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)triphenyl phosphonium bromide

Product 1

HCID 18381684HCID 18381684, compoundYield 34.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (5-methoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-triphenyl-phosphonium bromide (43.5 g, 0.0861 mole), prepared as described in example 36, and 4-pyridincarboxaldehyde (9.22 g, 0.0861 mole) in CH2Cl2 (300 ml) was dropwise added with triethylamine (12 ml, 0.0861 mole) while controlling the temperature in water bath. After 1 night under stirring at room temperature, the mixture was washed with water, discoloured, anhydrified and dried. The residue was suspended in CH3OH (135 ml) and added with hydrazine monohydrate (12.55 ml, 0.2583 mole). The mixture was refluxed for 1 hour, then cooled in water/ice, filtered and dried. The residue was crystallised in CH3OH to give 8 g of the title compound. The mother liquors were dried and the residue triturated in CH3OH (50 ml) to give further 3.5 g of the title compound (total yield: 50%).

Workup

  1. washthe mixture was washed with water
  2. customdried
  3. temperatureThe mixture was refluxed for 1 hour
  4. filtrationfiltered
  5. customdried
  6. customThe residue was crystallised in CH3OH

Sources & evidence

ORD record
ord-055261682d014ee3b9ba6b6b58b91cb6
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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