Acetic Anhydride → 6-(2-Ethylaminophenyl)-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950115Notes

Reaction equation

HRID 1950115 reaction equation
COC1C=C2C(=CC=1)CC(C1C=CC=CC=1N)CC2.C(OC(=O)C)(=O)C.[OH:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[CH2:34][CH:33]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[NH:44][C:45](=O)[CH3:46])[CH2:32][CH2:31]2>N1C=CC=CC=1>[CH2:45]([NH:44][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=1[CH:33]1[CH2:32][CH2:31][C:30]2[CH:29]=[C:28]([OH:27])[CH:37]=[CH:36][C:35]=2[CH2:34]1)[CH3:46]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 230875022-(6-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamineHCID 66626221N-[2-(6-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]acetamide

Product 1

HCID 230874696-(2-Ethylaminophenyl)-5,6,7,8-tetrahydronaphthalen-2-ol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamine (3.7 g), acetic anhydride (19 ml) and pyridine (19 ml) was stirred for 1 hour at room temperature. The reaction solution was concentrated in vacuo, then ethyl acetate (20 ml) and chloroform (5 ml) were added thereto, the crystal that was precipitated was filtered and dried. Synthesized from the total amount of the resulting N-[2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]acetamide according to an analogous synthetic method to Example 364 described below, the total amount of N-[2-(6-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]acetamide was used according to an analogous synthetic method to Example 337 described below to provide the title compound (2.3 g).

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. additionethyl acetate (20 ml) and chloroform (5 ml) were added
  3. customthe crystal that was precipitated
  4. filtrationwas filtered
  5. customdried
  6. customSynthesized from the total amount of the resulting N-[2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]acetamide according to an analogous synthetic method to Example 364

Sources & evidence

ORD record
ord-e73bf81b3c2a426b96c99c6577093465
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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