Acetyl chloride → 7-Methoxy-2-acetamido-tetralin

HRID 2104261

Reaction equation

HRID 2104261 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([NH2:13])[CH2:10]2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[C:23](Cl)(=[O:25])[CH3:24]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([NH:13][C:23](=[O:25])[CH3:24])[CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 116080152-Amino-7-methoxytetralin

Product 1

HCID 100136977-Methoxy-2-acetamido-tetralin

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 7-methoxy-1,2,3,4-tetrahydronapthalen-2-ylamine (2.54 g; 14.3 mmol) in CH2Cl2 (20 mL) was added DIEA (3.4 mL) and the reaction mixture was cooled to 0° C. Acetyl chloride (1.22 mL; 17.1 mmol) was added dropwise at 0° C. and the reaction was allowed to warm to room temperature, then stirred for 18 h. The reaction mixture was diluted with CH2Cl2, washed with H2O, dried over Na2SO4, filtered and the solvent removed under reduced pressure to yield a crude solid. Purification by flash chromatography (SiO2) eluting with hexanes-EtOAc yielded N-(7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-acetamide as a white solid.

Workup

  1. temperatureto warm to room temperature
  2. washwashed with H2O
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customto yield a crude solid
  7. customPurification by flash chromatography (SiO2)
  8. washeluting with hexanes-EtOAc

Sources & evidence

ORD record
ord-fba4b43a2bb14a97a71c2613f8e0ec73
Source dataset
uspto-grants-2009_08
Patent number
US07576238B2

Linked notes

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