Hydrochloric Acid → HCID 18972533, compound

HRID 2395183Notes

Reaction equation

HRID 2395183 reaction equation
[CH2:1]([N:8]1[C:21]2[CH:20]=[CH:19][C:18]([O:22][CH3:23])=[C:17]([CH:24]=[O:25])[C:16]=2[S:15][C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([O:26][CH3:27])[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+].Cl>O1CCCC1>[CH2:1]([N:8]1[C:21]2[CH:20]=[CH:19][C:18]([O:22][CH3:23])=[C:17]([CH2:24][OH:25])[C:16]=2[S:15][C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([O:26][CH3:27])[CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 18972567HCID 18972567, compound

Product 1

HCID 18972533HCID 18972533, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude 10-benzyl-3,7-dimethoxy-phenothiazine-4-carbaldehyde obtained was dissolved in 150 ml of absolute tetrahydrofuran, whereupon the solution was treated at 0° with 31.5 ml of lithium borohydride solution (1M in tetrahydrofuran). The reaction mixture was brought slowly to room temperature, stirred for 1 hour and then poured into ice-water, and the pH was adjusted to 3-4 with 0.5N hydrochloric acid solution. The mixture was extracted with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulphate and evaporated. After chromatography on silica gel with ethyl acetate/hexane (1:2) 8.0 g (73.7%) of (10-benzyl-3,7-dimethoxy-phenothiazin-4-yl)-methanol were obtained as a white amorphous solid.

Workup

  1. customwas brought slowly to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe combined organic phases were washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-91a07b9648b449d6a233c2317a1e7473
Source dataset
uspto-grants-1998_09
Patent number
US05811548

Reaction notes

Loading…