Hydrochloric Acid → HCID 178507165, compound

HRID 248327Notes

Reaction equation

HRID 248327 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:14]2[C:15](=O)[CH2:16][CH2:17][CH2:18][C:13]=2[O:12][N:11]=1)([O-])=[O:2].Cl.O1CCCC1>[Pd].CO>[NH2:11][C:10]1[C:5]2[C:4]([N+:1]([O-:2])=[C:15]3[C:14]=1[C:13](=[O:12])[CH2:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 150440063-(2-Nitrophenyl)-6,7-dihydro-1,2-benzoxazol-4(5H)-one

Product 1

HCID 178507165HCID 178507165, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6,7-dihydro-3-(2-nitrophenyl)-1,2-benzisoxazole-4(5H)-one, (7.0 g), 5% palladium-on-carbon (0.7 g), 5% hydrochloric acid (11 ml), and tetrahydrofuran (200 ml) was hydrogenated at 50 psi. After one hr, methanol (1 l) was added, and the mixture was filtered through celite. The filtrate was concentrated, and the concentrate was flash chromatographed (silica, 3-20% methanol/ethyl acetate; 40% methanol/dichloromethane). The appropriate fractions were collected and concentrated. The residue was triturated with methanol/diethyl ether to yield 5.4 g (83%) of product, mp 290° C. (dec).

Workup

  1. filtrationthe mixture was filtered through celite
  2. concentrationThe filtrate was concentrated
  3. customchromatographed (silica, 3-20% methanol/ethyl acetate; 40% methanol/dichloromethane)
  4. customThe appropriate fractions were collected
  5. concentrationconcentrated
  6. customThe residue was triturated with methanol/diethyl ether

Sources & evidence

ORD record
ord-7caeb6b763b444adb98e645ee447009b
Source dataset
uspto-grants-1993_05
Patent number
US05210087

Reaction notes

Loading…