Resorcinol → HCID 12713133, compound

HRID 2050335Notes

Reaction equation

HRID 2050335 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)O.[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O>[CH2:9]([NH:16][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][CH:8]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 5054ResorcinolHCID 7504Benzylamine

Product 1

HCID 12713133HCID 12713133, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

According to this invention, water-soluble coumarins and azacoumarins having the structures: ##STR2## wherein R is CH3 or CF3 and wherein R1 is H or CH3 are prepared. The coumarins are prepared by means of a three step process involving (1) heating resorcinol and benzylamine to form 3-benzylaminophenol, (2) reacting the 3-benzylaminophenol with ethyl acetoacetate or ethyl trifluoroacetoacetate in the presence of anhydrous zinc chloride and absolute ethanol to form 7-benzylamino-4-methylcoumarin or 7-benzylamino-4-trifluoromethylcoumarin, (3) sulfonating the product of step (2) with oleum and (4) neutralizing the sulfonate formed in step (3) with sodium bicarbonate. The azacoumarins are prepared by a similar process except that 6-chloro-2-pyridinol and either benzylamine or benzylmethylamine are used as the starting compounds (the step (1) reactants).

Workup

  1. customare prepared
  2. customThe coumarins are prepared by means of a three step process

Sources & evidence

ORD record
ord-f0c853e82be94ee392679c1bb2a0fce3
Source dataset
uspto-grants-1980_04
Patent number
US04200753

Reaction notes

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