Sodium Hydroxide → HCID 21285208, compound

HRID 2231937Notes

Reaction equation

HRID 2231937 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=3)[C:14]([CH2:25][CH3:26])=[C:13]([CH2:27][O:28]C(=O)C)[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].COC1C=C(C2C3C(=CC(OC)=C(OC)C=3)C(CC)=C(COC(=O)CC)N=2)C=CC=1OC.[OH-].[Na+]>Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=3)[C:14]([CH2:25][CH3:26])=[C:13]([CH2:27][OH:28])[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21285199HCID 21285199, compoundHCID 21285200HCID 21285200, compound

Product 1

HCID 21285208HCID 21285208, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 394.0 g (0.926 M) of 1-(3,4-dimethoxyphenyl)-3-(acetoxymethyl)-4-ethyl-6,7-dimethoxy-isoquinoline (compound of Example 20) or 407.0 g (0.926 M) of 1-(3,4-dimethoxyphenyl)-3-propionyloxymethyl-4-ethyl-6,7-dimethoxy-isoquinoline (compound of Example 38) and 2.76 liters of 5% aqueous hydrochloric acid is refluxed for one hour. The reaction mixture is cooled, poured into 1.98 liters of an aqueous 10% solution of sodium hydroxide, cooled to 5° C., the crystals formed are filtered, washed with 4×300 ml of water and dried at 80° to 100° C., giving 365 to 375 g of a crude product, m. p. 160° to 163° C. This product is recrystallized from one liter of ethyl acetate. Yield 322.5 g (91.0%), m. p. 164° to 166° C.

Workup

  1. temperatureis refluxed for one hour
  2. temperatureThe reaction mixture is cooled
  3. customthe crystals formed
  4. filtrationare filtered
  5. washwashed with 4×300 ml of water
  6. customdried at 80° to 100° C.

Sources & evidence

ORD record
ord-ae814094e81543f681779c8dbf4f9617
Source dataset
uspto-grants-1988_11
Patent number
US04785104

Reaction notes

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