Oxalic Acid → HCID 18382024, compound

HRID 2297508Notes

Reaction equation

HRID 2297508 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=3)[NH:9][CH:8]=2)[CH2:2]1.[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH:23]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+].[C:44]([OH:49])(=[O:48])[C:45]([OH:47])=[O:46]>ClCCCl.C(O)C>[C:44]([OH:49])(=[O:48])[C:45]([OH:47])=[O:46].[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH2:23][N:1]1[CH2:5][CH2:4][CH:3]([CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=3)[NH:9][CH:8]=2)[CH2:2]1

Participants

8

Reactant 5

HCID 971Oxalic AcidHCID 7362FurfuralHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 15511271HCID 15511271, compound

Product 1

HCID 18382024HCID 18382024, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 702EthanolSolvent

Procedure

Under an inert atmosphere and at ambient temperature, 47.3 mmol (10 g) of 3-[3-pyrrolidinylmethyl]-1H-indole-5-carbonitrile (described in Preparation A) are dissolved in 650 ml of 1,2-dichloroethane, and then 47.3 mmol (4.26 g) of furaldehyde are added. Stirring is carried out for 10 minutes, and 66.2 mmol (13.79 g) of sodium triacetoxyborohydride are added. After 30 minutes at ambient temperature, 350 ml of saturated sodium hydrogen carbonate solution are added. The organic phase is separated off, washed with water and dried over magnesium sulphate. Purification is carried out by chromatography on silica using a mixture of dichloromethane/methanol/ammonia 98/2/0.2 as eluant. The compound obtained is converted into the salt by one equivalent of oxalic acid in ethanol.

Workup

  1. waitAfter 30 minutes at ambient temperature
  2. customThe organic phase is separated off
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customPurification
  6. additiona mixture of dichloromethane/methanol/ammonia 98/2/0.2 as eluant
  7. customThe compound obtained

Sources & evidence

ORD record
ord-a52e33ef4070407fa43743c1cc1dd7ef
Source dataset
uspto-grants-2002_12
Patent number
US06492366B1

Reaction notes

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