Sodium borohydride → HCID 9926681, compound

HRID 1463255Notes

Reaction equation

HRID 1463255 reaction equation
[CH3:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:13][C:14]3[NH:15][CH2:16][CH2:17][N:18]=3)[C:8]=2[Br:12])[N:3]=1.[BH4-].[Na+].CC1CNC2C(=CC=CC=2Br)N1NC1NCCN=1>C(O)(=O)C>[CH3:1][CH:2]1[CH2:11][NH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:13][C:14]3[NH:15][CH2:16][CH2:17][N:18]=3)[C:8]=2[Br:12])[NH:3]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 15675860HCID 15675860, compoundHCID 54360539HCID 54360539, compound

Product 1

HCID 9926681HCID 9926681, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-methyl-5-bromo-6-(2-imidazolin-2-ylamino) quinoxaline (40.5 mg, 0.132 mmol) in acetic acid was cooled to 10° C. and carefully treated with NaBH4 (5.0 mg, 0.132 mmol). The reaction mixture was stirred for 15 minutes before the solvent was removed in vacuo. The residue was dissolved in H2O, treated with solid NaOH to pH 13 and extracted with CHCl3. The combined organic extracts were dried over MgSO4 and concentrated in vacuo to yield a yellow oil. The crude material was chromatographed (SiO2, 80/20 CHCl3 /CH3OH saturated with NH3 (g)) to yield 21.8 mg (a yield of 53%) of a tan solid, mp 203-205° C. Using various analytical procedures, this tan solid was determined to be (±) 2-methyl-5-bromo-(2-imidazolin-2-ylamino)-1,2,3,4-tetrahydroquinoxaline.

Workup

  1. customwas removed in vacuo
  2. dissolutionThe residue was dissolved in H2O
  3. additiontreated with solid NaOH to pH 13
  4. extractionextracted with CHCl3
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto yield a yellow oil
  8. customThe crude material was chromatographed (SiO2, 80/20 CHCl3 /CH3OH saturated with NH3 (g))
  9. customto yield 21.8 mg (a yield of 53%) of a tan solid, mp 203-205° C

Sources & evidence

ORD record
ord-261aacdf94f24df1baa8ff9f11932789
Source dataset
uspto-grants-1994_04
Patent number
US05300504

Reaction notes

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