Potassium sodium tartarate → HCID 22408489, compound

HRID 2081690Notes

Reaction equation

[C:1]([N:4]([C:7]1[CH:8]=[C:9]2[C:20](=[CH:21][CH:22]=1)[C:12]1[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:11]=1[CH2:10]2)[CH2:5][CH3:6])(=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>O1CCCC1>[CH2:1]([N:4]([C:7]1[CH:8]=[C:9]2[C:20](=[CH:21][CH:22]=1)[C:12]1[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:11]=1[CH2:10]2)[CH2:5][CH3:6])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

5,10-Dihydro-2-(N-Acetyl-N-ethylamino)indeno[1,2-b]indole (0.5 g, 1.7 mM) in dry tetrahydrofuran (80 cm3), protected under an atmosphere of nitrogen, was treated with lithium aluminum hydride (0.3 g) during 1 hour. The reaction mixture was then heated to 50° C. for a further 1 hour, cooled, and saturated sodium potassium tartrate (5 cm3) added. The solvent layer was decanted from the aqueous residue, and the latter washed with tetrahydrofuran (3×8 cm3). The combined organic phase and washing were filtered through phase transfer paper and evaporated to yield a yellow solid. This was crystallised from 95% ethanol to afford the title compound 0.35 g as pale yellow prisms, M.p. 204°-206° C. After column chromatography (silica: ethyl acetate/60°-80° petrol), the M.p. of the compound was raised to 205°-206° C. (0.26 g, 55%).

Workup

temperaturecooled
customThe solvent layer was decanted from the aqueous residue
washthe latter washed with tetrahydrofuran (3×8 cm3)
washThe combined organic phase and washing
filtrationwere filtered through phase transfer paper
customevaporated
customto yield a yellow solid
customThis was crystallised from 95% ethanol

Sources & evidence

ORD record: ord-187a0eeef9ea431e89ef98a4551d3f59
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05185360

Reaction notes

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