Isonicotinaldehyde 1-oxide → N-(isoquinolin-3-yl)-2-(4-pyridylmethyl)aminobenzoic acid amide-N-oxide

HRID 2373299Notes

Reaction equation

HRID 2373299 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12](=[O:19])[C:13]2C=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:2]=1.[N+:20]1([O-])[CH:25]=[CH:24][C:23]([CH:26]=O)=[CH:22][CH:21]=1.[C:29]([BH3-])#[N:30].[Na+].C(=O)(O)[O-:34].[Na+]>CO.C(OCC)(=O)C.C(O)(=O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH+:11]([O-:34])[C:12](=[O:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:29]=2[NH:30][CH2:26][C:23]2[CH:22]=[CH:21][N:20]=[CH:25][CH:24]=2)[N:2]=1

Participants

8

Reactant 4

HCID 81636Isonicotinaldehyde 1-oxideHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 12042972HCID 12042972, compound

Product 1

HCID 86596455N-(isoquinolin-3-yl)-2-(4-pyridylmethyl)aminobenzoic acid amide-N-oxideYield 71%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.05 g (4 mmol) of N-(isoquinolin-3-yl)benzoic acid amide is mixed in 48 ml of methanol with 788 mg (6.4 mmol) of 4-pyridine carbaldehyde-N-oxide and with 0.24 ml of glacial acetic acid, and it is stirred for 24 hours at room temperature. 404 mg of sodium cyanoborohydride is then added to this solution in portions, and it is stirred for another 5 hours at room temperature. After standing overnight, it is mixed with 50 ml of dilute sodium bicarbonate solution and shaken out three times with 50 ml each of ethyl acetate. The collected organic phase is washed with water, dried, filtered and concentrated by evaporation. The residue is absorptively precipitated in a little ethyl acetate and suctioned off. 1.05 g (71% of theory) of N-(isoquinolin-3-yl)-2-(4-pyridylmethyl)aminobenzoic acid amide-N-oxide with a melting point of 212.2° C. is obtained.

Workup

  1. stirringis stirred for another 5 hours at room temperature
  2. waitAfter standing overnight
  3. washThe collected organic phase is washed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe residue is absorptively precipitated in a little ethyl acetate

Sources & evidence

ORD record
ord-1b1f36aacbe74f24995c6041caaee50d
Source dataset
uspto-grants-2008_12
Patent number
US07459470B2

Reaction notes

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