Sodium borohydride → HCID 13355660, compound

HRID 1111966Notes

Reaction equation

HRID 1111966 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[C:9]([C:10]#[N:11])=[CH:8][C:7]([C:12](=[O:18])[CH2:13][NH:14][CH:15]2[CH2:17][CH2:16]2)=[CH:6][C:5]=1[Br:19]>O1CCCC1.O>[NH2:3][C:4]1[C:9]([C:10]#[N:11])=[CH:8][C:7]([CH:12]([OH:18])[CH2:13][NH:14][CH:15]2[CH2:16][CH2:17]2)=[CH:6][C:5]=1[Br:19]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 13355652HCID 13355652, compound

Product 1

HCID 13355660HCID 13355660, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3 gm of sodium borohydride were added at room temperature to a solution of 7.5 gm of 4'-amino-3'-bromo-5'-cyano-2-cyclopropylamino-acetophenone in 200 ml of tetrahydro-furan and 100 ml of water, and the mixture was stirred for one hour. Thereafter, the excess sodium borohydride was destroyed by addition of acetone. The insoluble part of the mixture was filtered off, and the solvents were distilled out of the filtrate in vacuo. The residue was dissolved in hot isopropanol, and the hydrochloride of 1-(4'-amino-3'-bromo-5'-cyano-phenyl)-2-cyclopropylanino-ethanol was precipitated by addition of isopropanolic hydrochloric acid, and recrystallized from isopropanol. M.p. 190°-193° C. (decomp.).

Workup

  1. customThereafter, the excess sodium borohydride was destroyed by addition of acetone
  2. filtrationThe insoluble part of the mixture was filtered off
  3. distillationthe solvents were distilled out of the filtrate in vacuo
  4. dissolutionThe residue was dissolved in hot isopropanol
  5. customthe hydrochloride of 1-(4'-amino-3'-bromo-5'-cyano-phenyl)-2-cyclopropylanino-ethanol was precipitated by addition of isopropanolic hydrochloric acid
  6. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-94fbaf1d7ef84cdeb3fded3c5a8d5493
Source dataset
uspto-grants-1978_10
Patent number
US04119710

Reaction notes

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