Formic Acid → 6-(4-Methoxy-2-methylaminophenyl)-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950111Notes

Reaction equation

HRID 1950111 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([OH:20])[CH:14]=[CH:13][C:12]=2[CH2:11]1.[CH:21](O)=O>C(=O)(O)[O-].[Na+]>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]([CH:10]2[CH2:19][CH2:18][C:17]3[CH:16]=[C:15]([OH:20])[CH:14]=[CH:13][C:12]=3[CH2:11]2)=[C:2]([NH:1][CH3:21])[CH:7]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 230873286-(2-Amino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-ol

Product 1

HCID 230873276-(4-Methoxy-2-methylaminophenyl)-5,6,7,8-tetrahydronaphthalen-2-ol

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 6-(2-amino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-ol (800 mg) and formic acid (8 ml) was refluxed overnight. The reaction mixture was diluted with a saturated aqueous solution of sodium bicarbonate, extracted with ethyl acetate, then washed with brine, dried over anhydrous magnesium sulfate, then the solvent was evaporated in vacuo. Synthesized from the resulting residue according to an analogous synthetic method to Example 337 described below, the title compound (730 mg) was obtained.

Workup

  1. temperaturewas refluxed overnight
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customSynthesized from the resulting residue

Sources & evidence

ORD record
ord-c12cd52837a64f59971099e6463a5dee
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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