Sodium borohydride → HCID 516469, compound

HRID 1263452Notes

Reaction equation

HRID 1263452 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-5bc0af72d9954a84a754c2fa922a8a9f
Source dataset
uspto-grants-2003_04
Patent number
US06541470B1

Reaction notes

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