HCID 3149442, compound → HCID 59513121, compound

HRID 1158597Notes

Reaction equation

HRID 1158597 reaction equation
[N+:1]([C:4]1[CH:34]=[CH:33][C:7]([C:8]([O:10][C:11]2[C:20]3[C:15](=[C:16]([O:21][C:22](=[O:32])[C:23]4[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=4)[CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.[H][H]>CN(C=O)C.[Pd]>[NH2:29][C:26]1[CH:25]=[CH:24][C:23]([C:22]([O:21][C:16]2[C:15]3[C:20](=[C:11]([O:10][C:8](=[O:9])[C:7]4[CH:33]=[CH:34][C:4]([NH2:1])=[CH:5][CH:6]=4)[CH:12]=[CH:13][CH:14]=3)[CH:19]=[CH:18][CH:17]=2)=[O:32])=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 3149442HCID 3149442, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59513121HCID 59513121, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

22.2 g of 5-[(4-nitrobenzoyl)oxy]-1-naphthyl 4-nitrobenzoate (48.4 mM) were suspended in 400 ml of DMF and 2.5 g of palladium on charcoal (10%) were added. The resulting mixture was hydrogenated at atmospheric pressure until the theoretical amount of hydrogen was consumed. The mixture was then filtered, the cake was washed with DMF and the filtrate was poured onto 4 L of water. The resulting suspension was stirred for 10 min. and the solids ware filtered off, washed with water and dried to give 16.0 g (40.2 mM, 83.0%) of 5-[(4-aminobenzoyl)oxy]-1-naphthyl 4-aminobenzoate as beige crystals.

Workup

  1. customwas consumed
  2. filtrationThe mixture was then filtered
  3. washthe cake was washed with DMF
  4. additionthe filtrate was poured onto 4 L of water
  5. filtrationthe solids ware filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-37dda5b94716452fae352d60ea699506
Source dataset
uspto-grants-2010_10
Patent number
US07811642B2

Reaction notes

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