Boron tribromide → HCID 17977677, compound

HRID 274475Notes

Reaction equation

HRID 274475 reaction equation
B(Br)(Br)[Br:2].Br.[NH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:27])[C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[C:18]([OH:24])=[C:17]([O:25]C)[CH:16]=1>C(Cl)Cl>[BrH:2].[NH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:27])[C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[C:18]([OH:24])=[C:17]([OH:25])[CH:16]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21459101HCID 21459101, compound

Product 1

HCID 17977677HCID 17977677, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.25 g of boron tribromide are added -20° to a suspension of 392.3 mg of N-(6-aminohexyl)-4-hydroxy-5-nitro-m-anisamide hydrobromide in 25 ml of dry methylene chloride. After the addition the mixture is stirred at -20° for 1 hour and subsequently at room temperature for 17 hours. The reaction mixture is then evaporated, the residue is treated with 10 ml of water and stirred at room temperature for 1 hour. After evaporating the water the residue is chromatographed on Sephadex LH 20 with toluene/ethanol (1:1). There is obtained N-6-aminohexyl-3,4-dihydroxy-5-nitrobenzamide hydrobromide of m.p. 205°-207° (from ethanol).

Workup

  1. additionAfter the addition the mixture
  2. customThe reaction mixture is then evaporated
  3. additionthe residue is treated with 10 ml of water
  4. stirringstirred at room temperature for 1 hour
  5. customAfter evaporating the water the residue
  6. customis chromatographed on Sephadex LH 20 with toluene/ethanol (1:1)

Sources & evidence

ORD record
ord-096d8f8a0e854478ad0525e626ff96b2
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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