Urea → HCID 178487123, compound

HRID 470322Notes

Reaction equation

HRID 470322 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[CH2:8][CH2:7][CH2:6]2.[NH2:14][C:15]([NH2:17])=[O:16].[CH2:18](OC(OCC)OCC)C>CS(O)(=O)=O.C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:9]3[N:17]=[C:15]([OH:16])[N:14]=[CH:18][C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 1176UreaHCID 141126-Methoxy-alpha-tetraloneHCID 31214Ethyl orthoformate

Product 1

HCID 178487123HCID 178487123, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-Methoxy-3,4-dihydro-2H-naphthalen-1-one (90 g, 0.511 M), urea (30.7 g, 0.511 M), triethylorthoformate (159 g, 1.07 M), ethanol (300 ml) and methane sulfonic acid (300 drops) was heated in the microwave at 90° C. for 1 hr. then cooled to room temperature. The solvent was removed under reduced pressure and the residue dried under vaccuo. The solid residue was then suspended in ethanol (250 ml) cooled to 0° C. and the precipitate was isolated via filtration and washed with ethanol (2×50 ml) and dried in vaccuo to give 8-Methoxy-5,6-dihydro-benzo[h]quinazolin-2-ol (43.95 g, 38% yield as a 1:1 urea complex) ES-MS MH+ 229.3 1H NMR (300 MHz, ppm, DMSO-d6): 11.45 (br S, 1H), 8.08 (d, 1H), 7.76 (br S, 1H), 6.95 (d, 1H), 6.91 (s, 1H), 5.4 (br S, 6H), 3.83 (s, 3H), 2.85 (m, 2H), 2.66 (m, 2H).

Workup

  1. temperaturethen cooled to room temperature
  2. customThe solvent was removed under reduced pressure
  3. customthe residue dried under vaccuo
  4. temperaturecooled to 0° C.
  5. customthe precipitate was isolated via filtration
  6. washwashed with ethanol (2×50 ml)
  7. customdried in vaccuo

Sources & evidence

ORD record
ord-ce6acb0576e242798452f72656c31a91
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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