Methyl 2-isocyanato-3-phenylpropanoate → HCID 178470451, compound

HRID 442341

Reaction equation

HRID 442341 reaction equation
[N:1]([CH:4]([C:12]([O:14][CH3:15])=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[C:2]=[O:3].[NH2:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[N:22][C:21]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:20]2[OH:32]>N1C=CC=CC=1>[OH:32][C:20]1[C:19]2[C:24](=[CH:25][CH:26]=[C:17]([NH:16][C:2]([NH:1][CH:4]([C:12]([O:14][CH3:15])=[O:13])[CH2:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)=[O:3])[CH:18]=2)[N:23]=[N:22][C:21]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

4

Reactant 2

HCID 2769481Methyl 2-isocyanato-3-phenylpropanoateHCID 178470447HCID 178470447, compound

Product 1

HCID 178470451HCID 178470451, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Isocyanato-1-methoxycarbonyl-2-phenylethane (1.2 g.) was added to a stirred solution of ethyl 6-amino-4-hydroxycinnolin-3-yl carboxylate (1.17 g.) in pyridine (20 ml.). The mixture was stirred overnight and the solid which separated was washed successively with pyridine (10 ml.) and ether (100 ml.). The solid was dissolved in boiling ethanol (1 l.), and the solution was filtered whilst hot. The filtrate was evaporated to approximately 300 ml. After standing at 0° C. overnight, the mixture was filtered and the solid residue washed successively with ethanol (50 ml.) and ether (100 ml.) to give ethyl 4-hydroxy-6-[3-(α-methoxycarbonylphenethyl)ureido]cinnolin-3-yl carboxylate, m.p. 242°-243° C.

Workup

  1. customthe solid which separated
  2. washwas washed successively with pyridine (10 ml.) and ether (100 ml.)
  3. dissolutionThe solid was dissolved
  4. filtrationthe solution was filtered whilst hot
  5. customThe filtrate was evaporated to approximately 300 ml
  6. waitAfter standing at 0° C. overnight
  7. filtrationthe mixture was filtered
  8. washthe solid residue washed successively with ethanol (50 ml.) and ether (100 ml.)

Sources & evidence

ORD record
ord-b2cc4793090c40cdb214bfcdf265bfe9
Source dataset
uspto-grants-1977_08
Patent number
US04045439

Linked notes

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