Ammonia → HCID 21416718, compound

HRID 1657418Notes

Reaction equation

HRID 1657418 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][C:16]([O:24][CH3:25])=[C:17]([O:22][CH3:23])[CH:18]=3)[CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([O:28][CH3:29])=[C:7]([O:26][CH3:27])[CH:8]=2)[N:3]=1.[NH3:30]>C(O)C>[NH2:30][C:2]1[N:11]=[C:10]([N:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][C:16]([O:24][CH3:25])=[C:17]([O:22][CH3:23])[CH:18]=3)[CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([O:28][CH3:29])=[C:7]([O:26][CH3:27])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 15288456HCID 15288456, compound

Product 1

HCID 21416718HCID 21416718, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product of (A), viz, 2-chloro-6,7-dimethoxy-4-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)quinazoline (5.0 g.) and a saturated solution of ammonia in ethanol (60 ml.) were heated together in an autoclave at 100°C. for a period of approximately 16 hours. After the reaction mixture had been allowed to cool to room temperature (~26°C.), the solvent was removed by means of evaporation under reduced pressure and the resulting brown residue (5.0 g.) was partitioned between methylene chloride and water. The separated organic layer thus obtained was then evaported in vacuo and the residue (3.0 g.) was subsequently converted into the hydrochloride salt by conventional means. Recrystallization of the crude material from a mixture of e thanol and isopropanol then afforded 1.0 g. of pure final product as the hydrochloride hemihydrate, m.p. 245°C.

Workup

  1. customthe solvent was removed by means of evaporation under reduced pressure
  2. customthe resulting brown residue (5.0 g.) was partitioned between methylene chloride and water
  3. customThe separated organic layer thus obtained
  4. customRecrystallization of the crude material
  5. additionfrom a mixture of e thanol and isopropanol
  6. customthen afforded 1.0 g

Sources & evidence

ORD record
ord-37617bc63c704e0ea104499f5f040955
Source dataset
uspto-grants-1976_06
Patent number
US03960861

Reaction notes

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