2-Methoxyethanol → HCID 15219320, compound

HRID 484375Notes

Reaction equation

HRID 484375 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1Cl)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17](Cl)=[C:16]([NH2:21])[CH:15]=2)[CH:8]=1)=[O:6].C([O-])=O.[Na+].COCCO>[Pd].O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13](=[O:22])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH2:21])[CH:15]=2)[CH:8]=1)=[O:6]

Participants

6

Reactant 3

HCID 80192-MethoxyethanolHCID 2723810Sodium FormateHCID 15219319(1,3-Phenylene)bis[(3-amino-4-chlorophenyl)methanone]

Product 1

HCID 15219320HCID 15219320, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

In the next step, to a sealed glass reaction vessel equipped with a thermometer, stirrer and reflux condenser, 156 g (0.41 mole) of the above 1,3-bis(3-amino-4-chlorobenzoyl)benzene, 145 g (2.13 mole) of sodium formate, 787 g of 2-methoxyethanol and 43 g of water were charged and heated to 100° C. with stirring. Successively, 7.8 g of a 5% palladium/activated carbon catalyst (a product of M.E. Chemcat Co.) was gradually added and the reaction was continued at 100° C. for 3 hours with stirring. The reaction mixture was cooled to 85° C. and hot filtered to remove the catalyst. The filtrate was poured into 4 l of water. The precipitated yellow crystals were filtered, washed with water and dried. Crude crystal of the desired 1,3-bis(3-aminobenzoyl)benzene were thus obtained in an amount of 126 g (97% yield). The crystals were analyzed by high performance liquid chromatography and determined to have a purity of 85.3%. The crude 1,3-bis(3-aminobenzoyl) benzene was dissolved in 630 g of toluene by heating and hot filtered to remove insoluble matter. Successively, 89 g of a 36% aqueous hydrochloric acid solution was added to the filtrate and allowed to cool. The precipitated crystal of 1,3-bis(3-aminobenzoyl)benzene hydrochloride was recrystallized from ethanol to obtain crystals of pure 1,3-bis(3-aminobenzoyl)benzene hydrochloride. The hydrochloride was dissolved in 1 l of water and neutralized with an aqueous ammonia solution. The precipitated yellow crystals were filtered, washed with water and dried. The desired product, crystals of pure 1,3-bis(3-aminobenzoyl)benzene were thus obtained in an amount of 85g (67% yield). Melting point was 114.2°~116.9° C.

Workup

  1. customIn the next step, to a sealed glass reaction vessel
  2. customequipped with a thermometer, stirrer
  3. temperaturereflux condenser
  4. addition) was gradually added
  5. stirringwith stirring
  6. temperatureThe reaction mixture was cooled to 85° C.
  7. filtrationhot filtered
  8. customto remove the catalyst
  9. additionThe filtrate was poured into 4 l of water
  10. filtrationThe precipitated yellow crystals were filtered
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-12bcd04d2e3647ca9b058ef4bb7225b2
Source dataset
uspto-grants-1993_07
Patent number
US05231160

Reaction notes

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