Hydrochloric Acid → HCID 14302393, compound

HRID 1200254Notes

Reaction equation

HRID 1200254 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][C:12]2[N:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:5]=1.[OH-].[Na+].O1CCCC1.Cl>O>[N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[N:21][C:12]=1[CH2:11][O:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:22])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 14302392HCID 14302392, compound

Product 1

HCID 14302393HCID 14302393, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.50 g (0.01869 moles) of 3-(2-quinazolinylmethoxy)benzoic acid methyl ester, 30.1 ml (0.0301 moles) of 1N sodium hydroxide and 22 ml of tetrahydrofuran is heated at reflux for 50 minutes. The mixture is allowed to come to room temperature and evaporated in vacuo giving a solid residue. After the addition of water and filtration through Celite the filtrate is acidified with 2.4M hydrochloric acid. The resulting precipitate is filtered, washed with water until the washings are pH 6. The precipitate is dried overnight in a vacuum desiccator and azeotroped with toluene on a rotoevaporator. Drying in vacuo gives the title compound, 4.75 g colorless solid, m.p. 221°-224° C.; IR (KBr) 1695, 1576, 1285, 1220 cm-1 ; NMR (DMOS-d6) 9.73 (s, 1H), 7.34-8.22 (8H, aromatic) 5.56 (2H, s), 3.43 (1H, broad).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 50 minutes
  3. customto come to room temperature
  4. customevaporated in vacuo
  5. customgiving a solid residue
  6. filtrationThe resulting precipitate is filtered
  7. washwashed with water until the washings
  8. customThe precipitate is dried overnight in a vacuum desiccator
  9. customazeotroped with toluene on a rotoevaporator
  10. customDrying in vacuo

Sources & evidence

ORD record
ord-fe998d9c65db40a18ec0578844e11176
Source dataset
uspto-grants-1990_02
Patent number
US04904786

Reaction notes

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