Water → HCID 23087191, compound

HRID 1950290Notes

Reaction equation

HRID 1950290 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=3)[CH2:11]2)=[C:7]([NH2:9])[CH:8]=1.[OH:22][C:23]1[CH:24]=[C:25]([C:32](O)=[O:33])[C:26](=[CH:30][CH:31]=1)[C:27](O)=[O:28].O>C(O)(=O)C>[OH:22][C:23]1[CH:24]=[C:25]2[C:26](=[CH:30][CH:31]=1)[C:27](=[O:28])[N:9]([C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[CH:10]1[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=3)[CH2:11]1)[C:32]2=[O:33]

Participants

5

Reactant 3

HCID 962WaterHCID 118814-Hydroxyphthalic acidHCID 230872055-Methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamine

Product 1

HCID 23087191HCID 23087191, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

A suspension of 5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamine (1.0 g) and 4-hydroxyphthalic acid (1.0 g) in acetic acid (10 ml) was stirred for 1 hour at 140° C. Water was added thereto followed by stirring, the solution was extracted with ethyl acetate, then sequentially washed with a saturated aqueous solution of sodium bicarbonate, water and brine, and the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (1.5 g).

Workup

  1. stirringby stirring
  2. extractionthe solution was extracted with ethyl acetate
  3. washsequentially washed with a saturated aqueous solution of sodium bicarbonate, water and brine
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-571e66002fce463f8aa36baede486776
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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