Hydrochloric Acid → 7-Chloro-1,3,4,5-tetrahydro-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one

HRID 35522Notes

Reaction equation

HRID 35522 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][CH:10]([CH:19]([C:24]([O:26][CH3:27])=[O:25])[C:20](OC)=[O:21])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1.C[O-].[Na+].Cl>CO>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:20](=[O:21])[CH:19]([C:24]([O:26][CH3:27])=[O:25])[CH:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[CH2:9][C:3]=2[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 14156189[2-(2-Amino-5-chlorophenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester

Product 1

HCID 141561947-Chloro-1,3,4,5-tetrahydro-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-oneYield 91.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of [2-(2-amino-5-chlorophenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester (23.2 g, 59.2 mmole) in methanol (200 ml) was added a 25% solution of sodium methoxide in methanol (16 ml, 69.97 mmole). The solution was refluxed for 3 hours under argon. The reaction was cooled to room temperature and treated with 200 ml of 1N hydrochloric acid. The white precipitate was filtered and washed with water, methanol, and dried in vacuo to yield 19.5 g of the title compound, melting point 189°-190.5° C.

Workup

  1. temperatureThe solution was refluxed for 3 hours under argon
  2. filtrationThe white precipitate was filtered
  3. washwashed with water, methanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ba378ed7f98445bb9efca829e2937753
Source dataset
uspto-grants-1988_08
Patent number
US04767756

Reaction notes

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