Hydrochloric Acid → HCID 131717722, compound

HRID 1646961Notes

Reaction equation

HRID 1646961 reaction equation
N([O-])=[O:2].[Na+].[OH2:5].N[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]([N:17]3[C:21](=[O:22])[CH:20]([CH2:23][O:24][CH3:25])[O:19][CH-:18]3)=[CH:14]2)=[CH:9][CH:8]=1.Cl.[CH3:27]O>>[CH3:25][O:24][CH2:23][CH:20]1[O:19][CH-:18][N:17]([C:13]2[CH:12]=[CH:11][C:10]3[C:15](=[CH:16][C:7]([O:5][CH3:27])=[CH:8][CH:9]=3)[CH:14]=2)[C:21]1=[O:22].[OH:2][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]([N:17]3[C:21](=[O:22])[CH:20]([CH2:23][O:24][CH3:25])[O:19][CH-:18]3)=[CH:14]2)=[CH:9][CH:8]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962Water2×HCID 23668193Sodium NitriteHCID 178494737HCID 178494737, compound

Product 2

HCID 131717722HCID 131717722, compoundHCID 178494738HCID 178494738, compound

Procedure

A solution of 0.97 g of sodium nitrite is 6 ml of water is added dropwise at 0° to 5° C. to a mixture of 3.47 g of 3-(7-amino-2-naphthyl)-5-methoxymethyl-2-oxazolidone, 6 ml of water and 3.3 ml of conc. hydrochloric acid. After the mixture is stirred for a few minutes, 100 ml of methanol are added thereto. The mixture is stirred at room temperature for 7 hours and then allowed to stand in a refrigerator overnight. The reaction mixture is extracted with ethyl acetate and the extract is washed and dried. The aqueous layer is further extracted with chloroform and the extract is dried. The residue (1.88 g) is purified by silica gel column chromatography [solvent: ethyl acetate-hexane (1:1)]. 5-methoxymethyl-3-(7-methoxy-2-naphthyl)-2-oxazolidone [Example 14, m.p. 95.5°-96.5° C. (recrystallized from ethyl acetate-hexane)] and 3-(7-hydroxy-2-naphthyl)-5-methoxymethyl-2-oxazolidone [Example 15 , m.p. 155°-157° C. (recrystallized from ethyl acetate-hexane)] are obtained.

Workup

  1. stirringThe mixture is stirred at room temperature for 7 hours
  2. customto stand in a refrigerator overnight
  3. extractionThe reaction mixture is extracted with ethyl acetate
  4. washthe extract is washed
  5. customdried
  6. extractionThe aqueous layer is further extracted with chloroform
  7. customthe extract is dried
  8. customThe residue (1.88 g) is purified by silica gel column chromatography [solvent: ethyl acetate-hexane (1:1)]

Sources & evidence

ORD record
ord-fc6b7d9294f24f32831e563fa8b59949
Source dataset
uspto-grants-1993_01
Patent number
US05182296

Reaction notes

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