Acetic Acid → HCID 136116522, compound

HRID 249981Notes

Reaction equation

HRID 249981 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH:13]([CH3:15])[CH3:14])=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH:16]=O.C(O)(=O)C.C([O-])(=O)C.[Na+].Cl.[NH2:28]O>O>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH:13]([CH3:15])[CH3:14])=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[C:16]#[N:28]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 136101835HCID 136101835, compound

Product 1

HCID 136116522HCID 136116522, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

7-Hydroxy-4-(isopropylamino)quinazoline-6-carbaldehyde (310 mg, 1.34 mmol) is presented as an initial charge in acetic acid (7 mL, 81 mmol) and admixed with sodium acetate (366 mg, 3.3 mmol) and also hydroxylamine hydrochloride (186 mg, 2.68 mmol). The batch is stirred at 130° C. for 18 hours. After cooling to room temperature, the batch is diluted with water and extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate. Removal of the solvent and also chromatographic purification (silica gel, dichloromethane/methanol: 0→30% methanol) of the residue gives the desired product in 38% yield (116 mg).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. customRemoval of the solvent and also chromatographic purification (silica gel, dichloromethane/methanol: 0→30% methanol) of the residue

Sources & evidence

ORD record
ord-d68665b75f4e43a7ac0cde8ed3b667d5
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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