Hydrochloric Acid → HCID 59676065, compound

HRID 2040456Notes

Reaction equation

HRID 2040456 reaction equation
C[O:2][C:3]1[CH:21]=[CH:20][C:6]2[C:7]3[NH:8][C:9]4[C:14]([C:15]=3[CH2:16][S:17][C:5]=2[CH:4]=1)=[CH:13][C:12]([O:18]C)=[CH:11][CH:10]=4.Cl>>[CH:20]1[C:6]2[C:7]3[NH:8][C:9]4[C:14]([C:15]=3[CH2:16][S:17][C:5]=2[CH:4]=[C:3]([OH:2])[CH:21]=1)=[CH:13][C:12]([OH:18])=[CH:11][CH:10]=4

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 59676057HCID 59676057, compound

Product 1

HCID 59676065HCID 59676065, compound

Procedure

A mixture of 3,8-dimethoxy-6,11-dihydro-5-thia-11-aza-benzo[a]fluorene (805 mg, 2.69 mmol) and Py.HCl (3.11 g, 26.9 mmol, 10 eq.) was heated to 210° C. for 30 minutes. The reaction mixture was then partitioned between EtOAc and saturated NaHCO3 aqueous solution. The aqueous layer was extracted three times with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a crude material. The crude material was purified by silica gel (EtOAc to CH2Cl2: MeOH 5:1) to yield the title compound as a brown solid.

Workup

  1. customThe reaction mixture was then partitioned between EtOAc and saturated NaHCO3 aqueous solution
  2. extractionThe aqueous layer was extracted three times with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a crude material
  8. customThe crude material was purified by silica gel (EtOAc to CH2Cl2: MeOH 5:1)

Sources & evidence

ORD record
ord-7b0f021da5e94249aa455955dd32f668
Source dataset
uspto-grants-2013_11
Patent number
US08580840B2

Reaction notes

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