Hydrochloric Acid → HCID 178429868, compound

HRID 2244087Notes

Reaction equation

HRID 2244087 reaction equation
N[C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:12]3[C:20]4[CH2:19][C:18]([CH3:22])([CH3:21])[CH2:17][C:16](=[O:23])[C:15]=4[C:14]([CH3:24])=[CH:13]3)=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.Cl.C(OCC)(=[O:28])C.O>>[OH:28][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:12]3[C:20]4[CH2:19][C:18]([CH3:22])([CH3:21])[CH2:17][C:16](=[O:23])[C:15]=4[C:14]([CH3:24])=[CH:13]3)=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 22728543Water ethylacetateHCID 59213787HCID 59213787, compound

Product 1

HCID 178429868HCID 178429868, compoundYield 60%

Procedure

1-(4-Amino-quinazolin-7-yl)-3,6,6-trimethyl-1,5,6,7-tetrahydro-indol-4-one (0.2 g 0.62 mmol) is microwaved at 80 degrees Celsius for 300 seconds in the presence of excess 36% HCl. The crude product is taken up in ethyl acetate/water. The organic phase is dried over magnesium sulfate, filtered, concentrated and chromatographed to afford 1-(4-hydroxyquinazolin-7-yl)-3,6,6-trimethyl-6,7-dihydro-1H-indol-4(5H)-one as a solid (0.12 g, 60%). LC/MS m/z=322 [M+H]+.

Workup

  1. dry with materialThe organic phase is dried over magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customchromatographed

Sources & evidence

ORD record
ord-b886b9dd00154dcfa69525ada1dbd047
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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