Hydrazine hydrate (1:1) → HCID 14996899, compound

HRID 1769702Notes

Reaction equation

HRID 1769702 reaction equation
[O:1]=[C:2]([N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27][CH2:26]1)[CH2:3][N:4]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:5](=[O:18])[CH2:6][N:7]1[C:11](=[O:12])C2=CC=CC=C2C1=O.O.NN.[CH3:38][C:39]1[CH:40]=[C:41]([N:45]=C=O)[CH:42]=[CH:43][CH:44]=1>>[CH3:38][C:39]1[CH:40]=[C:41]([NH:45][C:11](=[O:12])[NH:7][CH2:6][C:5]([N:4]([CH2:3][C:2](=[O:1])[N:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][CH2:27][CH2:26]2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])[CH:42]=[CH:43][CH:44]=1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 69303m-Tolyl isocyanateHCID 14996897N-[2-(3,4-Dihydro-1(2H)-quinolinyl)-2-oxoethyl]-1,3-dihydro-1,3-dioxo-N-phenyl-2H-isoindole-2-acetamide

Product 1

HCID 14996899HCID 14996899, compoundYield 28.8%

Procedure

The procedure is analogous to that described in Example 23, but 3.1 g of N-[2-oxo-2-(1,2,3,4-tetrahydro-1-quinolyl)ethyl]-N-phenyl-2-phthalimidoacetamide, 0.69 g of hydrazine hydrate and 0.91 g of 3-methylphenyl isocyanate are used as the starting material. The product obtained is purified by chromatography on 25 g of silica (0.065-0.200 mm) contained in a column 1.7 cm in diameter [eluent: methylene chloride/ethyl acetate (80-20 by volume)], collecting 25 cm3 fractions. Fractions 12 to 23 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization from ethyl acetate, 0.9 g of 2-[3-(3-methylphenyl)ureido]-N-[2-oxo-2-(1,2,3,4-tetrahydro-1-quinolyl)ethyl]-N-phenylacetamide melting at 167° C. is obtained.

Workup

  1. customThe product obtained
  2. customis purified by chromatography on 25 g of silica (0.065-0.200 mm)
  3. customcollecting 25 cm3 fractions
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  5. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-cec6aabc4a30450cac43b680da1131fd
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

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