Hydrochloric Acid → Ethyl alpha-amino-9H-xanthene-9-acetate hydrochloride

HRID 258188Notes

Reaction equation

HRID 258188 reaction equation
[N+:1]([CH:4]([CH:10]1[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:17][C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6])([O-])=O.Cl.[Cl:25]CCl>C(O)C.[Pd]>[ClH:25].[NH2:1][CH:4]([CH:10]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=2[O:17][C:18]2[C:23]1=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 15290758Ethyl alpha-nitro-9H-xanthene-9-acetate

Product 1

HCID 67803757Ethyl alpha-amino-9H-xanthene-9-acetate hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl α-nitro-9H-xanthene-9-acetate (7.5 g, 24 mmol) is dissolved in 150 mL of ethanol and 2 mL of concentrated hydrochloric acid and hydrogenated over 1.0 g of 20% palladium on carbon (53 hours, 51 pounds per square inch (psi)). The filtered solution is stripped of solvent and washed with dichloromethane. This gives 4.83 g of the title compound. An additional crop, 0.61 g is obtained after cooling the dichloromethane wash. The crops are combined and used in the next step.

Workup

  1. washwashed with dichloromethane
  2. customAn additional crop, 0.61 g is obtained
  3. washwash

Sources & evidence

ORD record
ord-4ee2a1494d2a48998f1c77ee79e2c3a4
Source dataset
uspto-grants-1993_11
Patent number
US05264577

Reaction notes

Loading…