Hydrochloric Acid → HCID 178507165, compound

HRID 1769641Notes

Reaction equation

HRID 1769641 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 (1l) was added, and the mixture was filtered through celite. The flitrate 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 flitrate 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-de9ad2ac2972411d945b3ef5626f53fb
Source dataset
uspto-grants-1995_01
Patent number
US05382594

Reaction notes

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