2-Amino-4-Nitrophenol → HCID 18629909, compound

HRID 1059482Notes

Reaction equation

HRID 1059482 reaction equation
Cl.[C:2]([CH2:4][C:5](=[NH:8])[O:6][CH3:7])#[N:3].[N+:9]([C:12]1[CH:17]=C[C:15](O)=[C:14](N)[CH:13]=1)([O-:11])=[O:10]>CO>[N+:9]([C:12]1[C:17]2[N:8]=[C:5]([CH2:4][C:2]#[N:3])[O:6][C:7]=2[CH:15]=[CH:14][CH:13]=1)([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 36133892-Amino-4-NitrophenolHCID 12436302Ethanimidic acid, 2-cyano-, methyl ester, hydrochloride (1:1)

Product 1

HCID 18629909HCID 18629909, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of methyl cyanoacetimidate hydrochloride (43.47 g, 0.32 mole) and 4-nitro-2-aminophenol (24.9 g, 0.16 mole) in methanol (260 ml) was heated at reflux for 3 h. The mixture was placed in an ice bath for 30 minutes and was filtered. The solid material was suspended in water (300 ml), stirred for a few minutes and filtered. It was washed with water (200 ml) and air dried to give 4-nitro-2-benzoxazoleacetonitrile (27.38 g, 83%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. filtrationwas filtered
  4. filtrationfiltered
  5. washIt was washed with water (200 ml) and air
  6. customdried

Sources & evidence

ORD record
ord-433be1a8d98d4bf698b3f36f7c2ddc37
Source dataset
uspto-grants-2003_02
Patent number
US06521397B1

Reaction notes

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