Sodium Hydroxide → 6,7-Dimethoxy-2-methoxyimino-1,2,3,4-Tetrahydronaphthalene

HRID 1446926Notes

Reaction equation

HRID 1446926 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[OH-].[Na+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[CH2:15][C:14](=O)[CH2:13][CH2:12]2>O>[CH3:20][O:19][C:18]1[CH:17]=[C:16]2[C:11](=[CH:10][C:9]=1[O:8][CH3:7])[CH2:12][C:13](=[N:4][O:2][CH3:3])[CH2:14][CH2:15]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 6098446,7-Dimethoxy-2-tetralone

Product 1

HCID 538187636,7-Dimethoxy-2-methoxyimino-1,2,3,4-TetrahydronaphthaleneYield 89.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.56 g (6.7 mmol) of methoxylamine hydrochloride and 6.5 ml (6.5 mmol) of a 1 M aqueous solution of NaOH was added to 0.689 g (3.34 mmol) of 6,7-dimethoxy-2-tetralone (IV). While under a nitrogen atmosphere the mixture was warmed to ca. 100° for 15 minutes and then kept at 40° using an infrared lamp for 18 hours. Water was added to the mixture which was then extracted with ether. The combined extracts were dried (MgSO4) and the solvent was removed on a rotary evaporator, affording 0.700 g (89.2%) of brown oil: nmr (CDCl3) δ2.3-2.9 (m, 4H), 3.32 (S, 1H), 3.57 (S, 1H), 3.73 (S, 6H), 3.78 (S, 3H), 6.4-6.6 (m, 2H). The compound was used without further purification.

Workup

  1. temperatureWhile under a nitrogen atmosphere the mixture was warmed to ca. 100° for 15 minutes
  2. customkept at 40°
  3. customfor 18 hours
  4. extractionwas then extracted with ether
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customthe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-3c3e5cc9851641b5adce9db45e0fd9a1
Source dataset
uspto-grants-1982_02
Patent number
US04314082

Reaction notes

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