2-Nitrobenzaldehyde → HCID 28570297, compound

HRID 2359884Notes

Reaction equation

HRID 2359884 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][NH2:17].C(OCC)(OCC)OCC>ClCCl>[CH3:12][O:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][NH:17][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 111012-NitrobenzaldehydeHCID 31214Ethyl orthoformateHCID 812922-Methoxybenzylamine

Product 1

HCID 28570297HCID 28570297, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.0 g (66.17 mmol) 2-nitrobenzaldehyde, 9.08 g (66.17 mmol) 2-methoxybenzylamine and 100 mL triethyl orthoformate in 100 mL dichloromethane were stirred for approx. 24 hours at room temperature. The residue obtained after evaporation was dissolved in 190 mL ethanol and mixed by portions with a total of 5.02 g NaBH4 while stirring at room temperature. After approx. 1 hour, the mixture was poured into water, extracted three times with dichloromethane; the combined organic phases were dried with MgSO4, filtered and concentrated until dry; 18.36 g yellow oil. ESI-MS [M+H+]=273.15.

Workup

  1. customThe residue obtained
  2. customafter evaporation
  3. dissolutionwas dissolved in 190 mL ethanol
  4. additionmixed by portions with a total of 5.02 g NaBH4
  5. additionthe mixture was poured into water
  6. extractionextracted three times with dichloromethane
  7. dry with materialthe combined organic phases were dried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customuntil dry

Sources & evidence

ORD record
ord-6752524f05d8429fbcf052e19d753db7
Source dataset
uspto-grants-2014_04
Patent number
US08686002B2

Reaction notes

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