2-Nitrobenzaldehyde → HCID 5279141, compound

HRID 1642089Notes

Reaction equation

HRID 1642089 reaction equation
ClC1C=C(C=CC=1Cl)C([NH:7][CH:8]1[C:14](=[O:15])[NH:13][C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[C:10]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:9]1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[N+:44]([C:47]1[CH:54]=[CH:53][CH:52]=[CH:51][C:48]=1[CH:49]=O)([O-:46])=[O:45].C(=O)(O)[O-].[Na+]>ClCCl.C(O)(=O)C>[N+:44]([C:47]1[CH:54]=[CH:53][CH:52]=[CH:51][C:48]=1[CH2:49][NH:7][CH:8]1[C:14](=[O:15])[NH:13][C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[C:10]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:9]1)([O-:46])=[O:45]

Participants

7

Reactant 4

HCID 111012-NitrobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 5279119HCID 5279119, compound

Product 1

HCID 5279141HCID 5279141, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of Intermediate 3 (50 mg) and sodium (triacetoxy)borohydride (106 mg) in dichloromethane (6 ml) and acetic acid (1 ml) was treated with 2-nitro-benzaldehyde (45 mg). The resulting mixture was stirred under nitrogen for 18 h. Saturated sodium bicarbonate solution was carefully added, and the mixture extracted with dichloromethane. The organic layer was passed through a hydrophobic frit, and evaporated. The residue was then purified on a silica gel SPE cartridge. Gradient elution with 10-18% ethyl acetate in petrol gave the title compound as a colourless solid (33 mg) LC/MS RT=4.83 min Found ES+=387

Workup

  1. extractionthe mixture extracted with dichloromethane
  2. customevaporated
  3. customThe residue was then purified on a silica gel SPE cartridge
  4. washGradient elution with 10-18% ethyl acetate in petrol

Sources & evidence

ORD record
ord-0bf05fa2254943b9b52277a81edf5d0a
Source dataset
uspto-grants-2012_02
Patent number
US08119630B2

Reaction notes

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