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

HRID 580381Notes

Reaction equation

HRID 580381 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 1N hydrochloric acid. A 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. filtrationA white precipitate was filtered
  3. washwashed with water, methanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-6b30b817434540e0ac733b7b64725910
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

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