6-Methoxy-5-nitro-1,2,3,4-tetrahydronaphthalen-1-one → HCID 22244785, compound

HRID 891175

Reaction equation

HRID 891175 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:14]([O-:16])=[O:15])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([Li])=[C:21]([O:26][CH3:27])[C:20]=1[O:28][CH3:29]>>[OH:13][C:9]1([C:23]2[CH:22]=[C:21]([O:26][CH3:27])[C:20]([O:28][CH3:29])=[C:19]([O:18][CH3:17])[CH:24]=2)[C:10]2[C:5](=[C:4]([N+:14]([O-:16])=[O:15])[C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH2:6][CH2:7][CH2:8]1

Participants

3

Reactant 2

HCID 130673376-Methoxy-5-nitro-1,2,3,4-tetrahydronaphthalen-1-oneHCID 178506740HCID 178506740, compound

Product 1

HCID 22244785HCID 22244785, compoundYield 55%

Procedure

6-Methoxy-5-nitro-1-tetralone (21) (2.65 g, 12.0 mol) was added at −20° C. to the trimethoxyphenyllithium and stirring was continued for 2 h (−20° C. -RT). The mixture was partitioned between CH2Cl2 and water, the organic layer was dried over anhydrous sodium sulfate, and, after filtration, the organic layer was concentrated in vacuo, to afford 1-Hydroxy-6-methoxy-5-nitro-1-(3′,4′,5′-trimethoxyphenyl)tetralin (30) as a crude yellow oil. (GC-MS shows the yield is about 55%). This compound, without purification, was added to a refluxing mixture of acetic acid (10 mL) and water (80 mL), and iron (0.5 g) was added. After heating at reflux for 1 h, the mixture was partitioned between CH2Cl2 (3×100 mL) and water (100 mL). The organic layer was washed with NaHCO3 (sat.) and water (100 mL each), dried over anhydrous sodium sulfate, and, after filtration, the organic layer was concentrated in vacuo to provide a yellow oil. Purification by column chromatography afforded 5-Amino-6-methoxy-1-(3′,4′,5′-trimethoxyphenyl)-3,4-dihydronaphthalene (31):

Workup

  1. custom(−20° C. -RT)
  2. customThe mixture was partitioned between CH2Cl2 and water
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. filtrationafter filtration
  5. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-6bbfcb19611c44d39bcd2d06c9d4cf13
Source dataset
uspto-grants-2006_02
Patent number
US07001926B2

Linked notes

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