2-Chloroethyl chloroformate → 6-[2-(2-Hydroxyethylamino)-4-methoxyphenyl]-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950639Notes

Reaction equation

HRID 1950639 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.ClC([O:24][CH2:25][CH2:26]Cl)=O>N1C=CC=CC=1>[OH:24][CH2:25][CH2:26][NH: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

Participants

4

Reactant 2

HCID 123052-Chloroethyl chloroformateHCID 230873286-(2-Amino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-ol

Product 1

HCID 579337496-[2-(2-Hydroxyethylamino)-4-methoxyphenyl]-5,6,7,8-tetrahydronaphthalen-2-ol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of 6-(2-amino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-ol (1.6 g) in pyridine (6 ml) was added dropwise 2-chloroethyl chloroformate (1.4 ml) on an ice bath, and the solution was stirred for 6.5 hours. The solution was diluted with ice water, and then extracted with ethyl acetate. The solution was washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. To the residue were added potassium hydroxide (3.0 g) and ethylene glycol (15 ml), and the solution was heated for 3 hours at 180° C. The solution was diluted with ice water, and then extracted with ethyl acetate. The solution was washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (800 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe solution was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. additionTo the residue were added potassium hydroxide (3.0 g) and ethylene glycol (15 ml)
  6. additionThe solution was diluted with ice water
  7. extractionextracted with ethyl acetate
  8. washThe solution was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated in vacuo
  11. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-d67491d87c27454aa29a2ae9f083fd8a
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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