3-Hydroxy-4-nitrobenzaldehyde → HCID 178427952, compound

HRID 2218409Notes

Reaction equation

HRID 2218409 reaction equation
[Cl:1][C:2]1[C:3]([CH3:10])=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[OH:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])[CH:15]=O>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH3:10])=[C:4]2[N:9]=[C:15]([C:14]3[CH:17]=[CH:18][C:19]([N+:20]([O-:22])=[O:21])=[C:12]([OH:11])[CH:13]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 697123-Hydroxy-4-nitrobenzaldehydeHCID 445580925-Chloro-4-methylpyridine-2,3-diamine

Product 1

HCID 178427952HCID 178427952, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

5-Chloro-4-methylpyridine-2,3-diamine (prepared by a method similar to Example 206a) (2.0 g, 12.7 mmol) was dissolved in DMF (40 ml) and heated to 100° C. 3-Hydroxy-4-nitrobenzaldehyde (2.10 g, 12.7 mmol) dissolved in DMF (10 ml) was added slowly (10 min). Air was bubbled through the reaction mixture. After 16 h, the DMF was evaporated off and the residue was purified by column chromatography (EtOAc/methanol, 10:1) giving the title compound (0.7 g, 18%).

Workup

  1. additionwas added slowly (10 min)
  2. customAir was bubbled through the reaction mixture
  3. customthe DMF was evaporated off
  4. customthe residue was purified by column chromatography (EtOAc/methanol, 10:1)

Sources & evidence

ORD record
ord-ef82c4465db74d0b8163b76e3a2a5f0c
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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