Sodium borohydride → HCID 516469, compound

HRID 2215669Notes

Reaction equation

HRID 2215669 reaction equation
[CH2:1]([N:3]1[C:12]2[CH:11]=[CH:10][C:9]([CH:13]([CH3:15])[CH3:14])=[CH:8][C:7]=2[C:6](=[O:16])[C:5]2[C:17](=[O:24])[C:18]3[C:23]([C:4]1=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:2].[BH4-].[Na+]>>[CH2:1]([N:3]1[C:12]2[CH:11]=[CH:10][C:9]([CH:13]([CH3:15])[CH3:14])=[CH:8][C:7]=2[C:6](=[O:16])[C:5]2[CH:17]([OH:24])[C:18]3[C:23]([C:4]1=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:2]

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 21952567HCID 21952567, compound

Product 1

HCID 516469HCID 516469, compound

Procedure

To an ethanolic solution of 5-ethyl-8-isopropyl-5,10-dihydro-11H-indeno[1,2-b]quinolin-10,11-dione (500 mg, 1,58 mmol) was added sodium borohydride (62 mg, 1.64 mmol) in portions followed by stirring at room temperature for 1 hour. After removing ethanol, the reaction mixture was diluted with water and extracted with chloroform twice. The combined organic layers were washed with saturated sodium chloride solution and dried with sodium sulfate followed by evaporating to remove chloroform. The title compound was obtained by crystallizing the residue from acetone-diethyl ether mixture. 1H-NMR (CDCl3) δ 1.35 (6H, d, CH(CH3)2), 1.72 (3H, t, NCH2CH3), 3.11 (1H, septet, CH), 4.79 (2H, q, NCH2), 5.86 (1H, s, H-11), 7.52-7.63 (3H, m, Ar—H), 7.85 (1H, dd, H-9)

Workup

  1. customAfter removing ethanol
  2. additionthe reaction mixture was diluted with water
  3. extractionextracted with chloroform twice
  4. washThe combined organic layers were washed with saturated sodium chloride solution
  5. dry with materialdried with sodium sulfate
  6. customby evaporating
  7. customto remove chloroform

Sources & evidence

ORD record
ord-ac0b52c48f8c4a9f8f515317d73f1513
Source dataset
uspto-grants-2006_09
Patent number
US07109338B2

Reaction notes

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