Methanol → HCID 20558923, compound

HRID 354798Notes

Reaction equation

HRID 354798 reaction equation
Cl.[NH2:2][CH2:3][CH:4]([OH:15])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14].[C:16]1([C:22]2[N:31]=[C:30](Cl)[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CO.[OH-].[Na+]>O>[OH2:6].[CH3:14][O:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[O:6][CH2:5][CH:4]([OH:15])[CH2:3][NH:2][C:30]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[C:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:31]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 809774-Chloro-2-phenylquinazolineHCID 13760242HCID 13760242, compound

Product 1

HCID 20558923HCID 20558923, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture containing 5.8 g (0.025 mole) of 1-amino-3-ortho-methoxyphenoxy 2-propanol hydrochloride, 6 g (0.025 mole) of 2-phenyl-4-chloroquinazoline, 150 ml of methanol, 1.0 g of sodium hydroxide (in one ml of water) was refluxed for 6 hrs. Another one gram of sodium hydroxide (in one ml of water) was added and refluxing was continued for 2 hrs. The resulting reaction mixture was cooled to room temperature and filtered. The gummy substance which was obtained when the filtrate was mixed with 300 ml of water was separated, washed with water, then dissolved in acetone. The acetone solution was treated with one ml of 12 N hydrochloric acid and the white crystalline precipitate was separated, dissolved in water, adjusted to pH=7.5. A white crystalline solid was obtained. This crystalline solid was recrystallized with methanol and water to give 1.5 g of the title compound, m.p. 138°-140° C.

Workup

  1. temperaturewas refluxed for 6 hrs
  2. temperaturerefluxing
  3. customThe resulting reaction mixture
  4. filtrationfiltered
  5. customThe gummy substance which was obtained when the filtrate
  6. customwas separated
  7. washwashed with water
  8. dissolutiondissolved in acetone
  9. additionThe acetone solution was treated with one ml of 12 N hydrochloric acid
  10. customthe white crystalline precipitate was separated
  11. dissolutiondissolved in water
  12. customA white crystalline solid was obtained
  13. customThis crystalline solid was recrystallized with methanol and water

Sources & evidence

ORD record
ord-e8a6ae62886047dd80efc5f9afb3581f
Source dataset
uspto-grants-1983_03
Patent number
US04377582

Reaction notes

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