4-Nitroanthranilic acid → HCID 178526462, compound

HRID 1968632Notes

Reaction equation

HRID 1968632 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(O)(=O)C.[CH:18](N)=[NH:19]>C(O)C>[N+:11]([C:9]1[CH:10]=[C:2]2[C:3]([C:4]([OH:6])=[N:19][CH:18]=[N:1]2)=[CH:7][CH:8]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 120764-Nitroanthranilic acidHCID 160693Formamidine acetate

Product 1

HCID 178526462HCID 178526462, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-amino-4-nitrobenzoic acid (6.00 g, 32.94 mmol) in ethanol (40 mL) was added formamidin acetate (6.80 g, 65.32 mmol). The reaction mixture was refluxed for 5 h. The reaction mixture was cooled to room temperature and refrigerated. The precipitate was filtered out, washed with several portions of cooled ethanol, and then dried in vacuo to give 5.60 g (89%) of 7-nitroquinazolin-4-ol as a yellow solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. filtrationThe precipitate was filtered out
  3. washwashed with several portions of cooled ethanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-619de4870070485cb38144a82d5bb391
Source dataset
uspto-grants-2013_04
Patent number
US08426430B2

Reaction notes

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