4-Isopropoxybenzaldehyde → HCID 178487280, compound

HRID 1852084Notes

Reaction equation

HRID 1852084 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[O:12])O[C:9](=O)[NH:8][C:7]=2[CH:14]=1.[CH:15]([O:18][C:19]1[CH:26]=[CH:25][C:22](C=O)=[CH:21][CH:20]=1)([CH3:17])[CH3:16].C([O-])(=O)C.[NH4+:31]>CCO>[CH:15]([O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:9]2[N:31]=[C:11]([OH:12])[C:6]3[C:7](=[CH:14][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[NH:8]2)=[CH:21][CH:20]=1)([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 2500774-IsopropoxybenzaldehydeHCID 517165Ammonium AcetateHCID 143819977-Methoxy-2H-3,1-benzoxazine-2,4(1H)-dione

Product 1

HCID 178487280HCID 178487280, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

7-methoxy-1H-benzo[d][1,3]oxazine-2,4-dione (0.5 g, 2.59 mmol), 4-isopropoxybenzaldehyde (0.425 g, 2.59 mmol), and ammonium acetate (0.239 g, 3.11 mmol) were dissolved in EtOH (1 mL) and heated at 80° C. for 0.5 h. The solvent was removed under vacuum and the crude material was purified by silica gel chromatography using a gradient of 40-100% EtOAc in Hexanes. The product fractions were collected and concentrated under vacuum to give 2-(4-isopropoxyphenyl)-7-methoxy-1,2-dihydroquinazolin-4-ol (685 mg, 85% yield). MS: MS m/z 313.2 (M++1).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe crude material was purified by silica gel chromatography
  3. customThe product fractions were collected
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2ed68f31dcb148c290888695c7ed758b
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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