Ethanol → HCID 19381238, compound

HRID 2209533Notes

Reaction equation

HRID 2209533 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:21]3[C:20](=O)[CH2:19][CH2:18][CH2:17][C:16]=3[NH:15][C:14]3[CH2:13][CH2:12][CH2:11][C:10](=[O:23])[C:9]2=3)[CH:5]=[CH:6][CH:7]=1.C(O)C.[BH4-].[Na+]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:9]3[C:10](=[O:23])[CH2:11][CH2:12][CH2:13][C:14]=3[NH:15][C:16]3[CH2:17][CH2:18][CH2:19][CH2:20][C:21]2=3)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1350395HCID 1350395, compoundHCID 4311764Sodium borohydride

Product 1

HCID 19381238HCID 19381238, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred 70° C. mixture of 9-(3-bromophenyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione (5.0 g, 13.4), ethanol (120 mL) and pyridine (40 mL) was added sodium borohydride (7.5 g) in three portions over six hours. The solvent was removed; the resulting yellow solid washed well with water and air dried to provide the title compound (4.8 g). Recrystallization from ethanol/hexane returned analytically pure yellow solid, mp 258°-260° C.; NMR: 1.41-1.51 (m,3, CH2), 1.60-1.88 (m,5, CH2), 2.09-2.15 (m,4, CH2), 2.39-2.45 (m,2, CH2), 4.17 (s,1, CH), 7.16-7.21 (m,2, Ar), 7.26-7.29 (m,2, Ar), 8.44 (s,1, NH); (CI, CH4) MS: m/z=360(M+1). Analysis for C19H20BrNO: Calculated C, 63.69; H, 5.59; N, 3.91; Found: C, 63.73; H, 5.69; N, 3.94.

Workup

  1. customThe solvent was removed
  2. washthe resulting yellow solid washed well with water and air
  3. customdried

Sources & evidence

ORD record
ord-1e6c1c6c42d14d39bd7a2f0f1b6c0a75
Source dataset
uspto-grants-1995_10
Patent number
US05455253

Reaction notes

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