Ethyl 2-aminobenzoate → HCID 178515604, compound

HRID 638262Notes

Reaction equation

HRID 638262 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=O.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=O)[CH3:21])=[CH:16][CH:15]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C1(OC2C=CC=CC=2)C=CC=CC=1>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[C:4]([OH:6])[C:3]3[C:2](=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:1]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6877Ethyl 2-aminobenzoateHCID 7467P-ChloroacetophenoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 178515604HCID 178515604, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred mixture of 16.52 g (0.1 mol) of ethyl o-aminobenzoate, 15.46 g (0.1 mol) of p-choroacetophenone, and 250 ml of diphenyl ether was carefully added 18.67 g of aluminum chloride. This mixture was heated under reflux for 2 hr and then let cool to 60° C. The solids were collected and washed with 2×100 ml of toluene. These solids were triturated twice with a mixture of 500 ml of 6N hydrochloric acid and 50 ml of acetone. Each time the solids were collected they were washed with 100 ml of 6N hydrochloric acid, 3×100 ml of water, and 2×50 ml of acetone. There was obtained 22.34 g of the above-named product, mp 327-330.

Workup

  1. temperatureThis mixture was heated
  2. temperatureunder reflux for 2 hr
  3. customThe solids were collected
  4. washwashed with 2×100 ml of toluene
  5. customThese solids were triturated twice with a mixture of 500 ml of 6N hydrochloric acid and 50 ml of acetone
  6. customEach time the solids were collected they
  7. washwere washed with 100 ml of 6N hydrochloric acid, 3×100 ml of water, and 2×50 ml of acetone

Sources & evidence

ORD record
ord-2cf1213001c9406790adf6fc62e5a200
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

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