Hydrochloric Acid → HCID 178450041, compound

HRID 2300580Notes

Reaction equation

HRID 2300580 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:17]3[C:13]([C:14]([CH3:21])([CH3:20])[CH:15]([OH:19])[N+:16]=3[O-])=[CH:12][C:11](=[O:22])[C:10]=2[CH:23]=1)[CH2:2][CH2:3][CH3:4].Cl.C1(=O)C=CC(=[O:31])C=C1>CCO>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:17]3[C:13]([C:14]([CH3:21])([CH3:20])[C:15](=[O:19])[N:16]=3)=[C:12]([OH:31])[C:11](=[O:22])[C:10]=2[CH:23]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4650QuinoneHCID 18376534HCID 18376534, compound2×

Product 1

HCID 178450041HCID 178450041, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 7-Butoxy-2-hydroxy-3,3-dimethyl-2,3-dihydro-5H-benzo[g]indol-5-one 1-oxide (compound 6 prepared in step (ii) above)(13 mg, 0.036 mmol) in EtOH (2 mL) with conc. HCl in EtOH (0.5 mL) was heated at 60° for 1 h. The yellow solution turned red. When no starting material remained, benzoquinone (39 mg, 0.36 mmol) was added and the mixture was heated 1 h. The solvent was evaporated and the crude product was purified on RP-HPLC. Yield. 12 mg. (24%). 1H NMR (400 MHz, CDCl3) δ 1.00 (tr., 3H), 1.51 (m, 2 H), 1.55 (s, 6 H), 1.82 (m, 2 H), 4.10 (tr., 2H), 7.20 (dd, 1 H), 7.46 (d, 1 H), 7.70 (d, 1 H), 9.62 (br.s, 1 H). MS (EI) m/z 313 (M+).

Workup

  1. temperaturethe mixture was heated 1 h
  2. customThe solvent was evaporated
  3. customthe crude product was purified on RP-HPLC
  4. customYield

Sources & evidence

ORD record
ord-f8d53def878245dab7b7f15c9955bb33
Source dataset
uspto-grants-2002_12
Patent number
US06498182B2

Reaction notes

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