Hydrochloric Acid → HCID 13443699, compound

HRID 2260368Notes

Reaction equation

HRID 2260368 reaction equation
[CH3:1][C:2]1[CH2:3][CH:4]2[CH:9]([CH2:10][C:11]=1[CH3:12])[C:8](=[O:13])[C:7]([O:14][CH3:15])=[CH:6][C:5]2=[O:16].N#N.C([O-])([O-])=O.[K+].[K+].Cl>CO>[CH3:1][C:2]1[CH2:3][C:4]2[C:5]([OH:16])=[CH:6][C:7]([O:14][CH3:15])=[C:8]([OH:13])[C:9]=2[CH2:10][C:11]=1[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 947Nitrogen2×HCID 11430Potassium CarbonateHCID 13443680HCID 13443680, compound

Product 1

HCID 13443699HCID 13443699, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6,7-dimethyl-2-methoxy-4a,5,8,8a-tetrahydronaphthalene-1,4-dione (4.0 g, 18.2 mmol) in MeOH (600 mL) was purged with a stream of N2 for 10 min with stirring at rt. With continued N2 purging, solid K2CO3 (2.51 g, 18.2 mmol, Baker) was added to the stirred solution. The solution immediately turned yellow. The reaction was allowed to stir for 30 min at rt under N2, after which it was brown. To this there was added a dilute HCl solution (10% concd HCl, 90% H2O, 200 mL) in one portion. The MeOH was removed in vacuo to give a colorless suspension. The suspension was cooled in an ice bath for 20 min. The suspended material was collected by filtration, washed with a dilute acid solution (as above, 3×20 mL) and dried in vacuo to yield a fluffy colorless solid (3.90 g, 98%, pure by 1H NMR analysis (unstable on TLC)); mp 200-°201° C.; 1H NMR (CDCl3) δ1.79 (s, 6H), 3.12 (m, 2H), 3.25 (m, 2H), 3.83 (s, 3H), 4.25 (s, 1H), 5.25 (s, 1H), 6.35 (s, 1H).

Workup

  1. stirringto stir for 30 min at rt under N2
  2. customThe MeOH was removed in vacuo
  3. customto give a colorless suspension
  4. temperatureThe suspension was cooled in an ice bath for 20 min
  5. filtrationThe suspended material was collected by filtration
  6. washwashed with a dilute acid solution (as above, 3×20 mL)
  7. customdried in vacuo
  8. customto yield a fluffy colorless solid (3.90 g, 98%, pure by 1H NMR analysis (unstable on TLC))
  9. custommp 200-°201° C.

Sources & evidence

ORD record
ord-62ddbab410aa429181cb5fafca40aded
Source dataset
uspto-grants-1995_12
Patent number
US05476933

Reaction notes

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