Methyl 5-amino-2-(4-fluoro-2-hydroxyphenyl)-3-methylbenzoate → 8-Amino-3-fluoro-10-methylbenzo[c]chromen-6-one

HRID 1966276Notes

Reaction equation

HRID 1966276 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:20])[C:5]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[OH:19])=[C:6]([CH:11]=1)[C:7](OC)=[O:8]>N1C=CC=CC=1>[NH2:1][C:2]1[CH:3]=[C:4]([CH3:20])[C:5]2[C:12]3[C:13](=[CH:14][C:15]([F:18])=[CH:16][CH:17]=3)[O:19][C:7](=[O:8])[C:6]=2[CH:11]=1

Participants

3

Reactant 1

HCID 58027000Methyl 5-amino-2-(4-fluoro-2-hydroxyphenyl)-3-methylbenzoate

Product 1

HCID 580271338-Amino-3-fluoro-10-methylbenzo[c]chromen-6-oneYield 94%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl 5-amino-2-(4-fluoro-2-hydroxyphenyl)-3-methylbenzoate (Reference Compound No. 1-4-(5), 7.40 g, 26.9 mmol) was dissolved in pyridine (250 mL) and then the reaction mixture was refluxed overnight. The reaction mixture was concentrated under reduced pressure, then ethyl acetate-hexane (1:1) was added to the obtained residue, and then filtered to give the titled reference compound (6.15 g) as a pale yellow solid. (Yield 94%)

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionethyl acetate-hexane (1:1) was added to the obtained residue
  4. filtrationfiltered

Sources & evidence

ORD record
ord-18d3a7fae01847bb88826c8eb1cb50cf
Source dataset
uspto-grants-2013_04
Patent number
US08420635B2

Reaction notes

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