Hydrochloric Acid → HCID 21480576, compound

HRID 1490157Notes

Reaction equation

HRID 1490157 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]2[CH2:19][CH2:18][C:17]3[NH:16][C:15](=[O:20])[CH:14]([CH3:21])[CH2:13][C:12]=3[CH2:11]2)=[CH:5][CH:4]=1.B(Br)(Br)Br.Cl>ClCCl.CO>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH:10]2[CH2:19][CH2:18][C:17]3[NH:16][C:15](=[O:20])[CH:14]([CH3:21])[CH2:13][C:12]=3[CH2:11]2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 21480568HCID 21480568, compound

Product 1

HCID 21480576HCID 21480576, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

3,4,5,6,7,8-Hexahydro-6-((4-methoxyphenyl)methyl)-3-methylquinolin-2[1H]-one (2.85 g) prepared according to Example 1 (2.85 g) was suspended in dichloromethane (5 ml) and cooled with ice and boron tribromide (3.3 ml) was added. The mixture was left to stir until tlc (SiO2 /chloroform) showed no starting material remained and then the mixture was quenched by slow addition of water (10 ml). The reaction mixture was further diluted with water and the resulting solid was isolated by filtration. The solid was dissolved in methanol (100 ml) and concentrated HCl (1 ml) was added. The methanol was removed under reduced pressure and the procedure repeated three times. The solid was suspended in ethyl acetate, filtered and washed with ether to give the hemihydrate of the title compound (2.22 g), mp.230°-235° C.

Workup

  1. additionwas added
  2. waitThe mixture was left
  3. customthe mixture was quenched by slow addition of water (10 ml)
  4. additionThe reaction mixture was further diluted with water
  5. customthe resulting solid was isolated by filtration
  6. customThe methanol was removed under reduced pressure
  7. filtrationfiltered
  8. washwashed with ether

Sources & evidence

ORD record
ord-34ca0f3a49944023a14066249e50a98f
Source dataset
uspto-grants-1997_10
Patent number
US05681839

Reaction notes

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