Methanol → HCID 135589774, compound

HRID 384761Notes

Reaction equation

HRID 384761 reaction equation
[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:11])=O)[C:7]([NH2:13])=[CH:6][C:5]=1[O:14][CH2:15][CH2:16][CH2:17][OH:18])([O-:3])=[O:2].C([O-])([O-])OC.C([O-])(=O)C.[NH4+:28].[CH3:29]O>O>[N+:1]([C:4]1[CH:12]=[C:8]2[C:7](=[CH:6][C:5]=1[O:14][CH2:15][CH2:16][CH2:17][OH:18])[N:13]=[CH:29][NH:28][C:9]2=[O:11])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 517165Ammonium AcetateHCID 23032995HCID 23032995, compoundHCID 53629101Methylorthoformate

Product 1

HCID 135589774HCID 135589774, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 10-mL volume stainless steel pressure-resistant vessel were placed 0.65 g (2.5 mmol) of 5-nitro-4-(3-hydroxypropoxy)anthranilic acid, 1.06 g (10.0 mmol) of methyl orthoformate, 0.77 g (10.0 mmol) of ammonium acetate, and 6.0 mL of methanol. The reaction was carried out at 140° C. for 6.5 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and 50 mL of water was added to the reaction mixture. The precipitated crystalline product was collected by filtration and dried under reduced pressure to give 0.52 g (isolated yield: 79%) of 6-nitro-7-(3-hydroxypropoxy)quinazolin-4-one as a gray crystalline product.

Workup

  1. customIn a 10-mL volume stainless steel pressure-resistant vessel were placed
  2. filtrationThe precipitated crystalline product was collected by filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-854477b9d6ee488db4e62c1c97a0d1e8
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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