Tetrahydrofuran → HCID 13188751, compound

HRID 1158599Notes

Reaction equation

HRID 1158599 reaction equation
[N+:1]([C:4]1[CH:30]=[CH:29][C:7]([C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:28])[C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.C1COCC1.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:30]=[CH:29][C:7]([C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:28])[C:19]2[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=2)=[O:9])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 247241HCID 247241, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13188751HCID 13188751, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

40.1 g 6-[(4-nitrobenzoyl)oxy]hexyl 4-nitrobenzoate (96.3 mM) were suspended in 300 ml of ethyl acetate and 300 ml of THF and 4.0 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 evaporated. The residue was suspended in 200 of cyclohexane. It was stirred for 30 min. and then the solids were filtered off, washed with cyclohexane and dried to give 33.2 g (93.1 mM, 97%) of 6-[(4-aminobenzoyl)oxy]hexyl 4-aminobenzoate as beige crystals.

Workup

  1. customwas consumed
  2. filtrationThe mixture was then filtered
  3. washthe cake was washed with DMF
  4. customthe filtrate was evaporated
  5. filtrationthe solids were filtered off
  6. washwashed with cyclohexane
  7. customdried

Sources & evidence

ORD record
ord-72e3ce9cda7349b49988cf2de018bf65
Source dataset
uspto-grants-2010_10
Patent number
US07811642B2

Reaction notes

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