Hydrochloric Acid → HCID 15684552, compound

HRID 728148Notes

Reaction equation

HRID 728148 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]3[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]3[CH:19]=2)=[CH:4][C:3]=1[OH:20].[N:21]#[C:22]Br.Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O.C(OCC)(=O)C>[NH2:21][C:22]1[O:20][C:3]2[CH:4]=[C:5]([CH2:8][CH2:9][C:10]3[N:11]=[C:12]4[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]4[CH:19]=3)[CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 15684641HCID 15684641, compound

Product 1

HCID 15684552HCID 15684552, compoundYield 26.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-[2-(4-amino-3-hydroxyphenyl)ethyl]-7-methylimidazo[1,2-a]pyridine (1.5 g) and cyanogen bromide (0.7 g) in ethanol (25 ml) was stirred for 2 hours at ambient temperature. To the reaction mixture was added a mixture of ethyl acetate and water, and the mixture was adjusted to pH 1.0 with 10% hydrochloric acid. The separated aqueous layer was adjusted to pH 8.0 with potassium carbonate and the mixture was extracted with a solution of ethyl acetate and tetrahydrofuran. The extract was washed with brine and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was purified by alumina column chromatography eluting with a solution of chloroform and methanol (19:1, V/V). The fractions containing object compound were concentrated to give 2-amino-6-[2-(7-methylimidazo[1,2-a]pyridin-2-yl)ethyl]benzoxazole (0.44 g).

Workup

  1. additionTo the reaction mixture was added
  2. extractionthe mixture was extracted with a solution of ethyl acetate and tetrahydrofuran
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customgave a residue, which
  7. customwas purified by alumina column chromatography
  8. washeluting with a solution of chloroform and methanol (19:1, V/V)
  9. additionThe fractions containing object compound
  10. concentrationwere concentrated

Sources & evidence

ORD record
ord-7178477c224c4834906fdee010b95f09
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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