2-Aminobenzyl alcohol → HCID 13730769, compound

HRID 980532Notes

Reaction equation

HRID 980532 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].Br[C:11]1[C:12](=[O:24])[N:13]([C:17]([CH:21]([CH3:23])[CH3:22])([CH3:20])[C:18]#[N:19])[C:14](=[O:16])[CH:15]=1>C(O)C>[C:18]([C:17]([N:13]1[C:12](=[O:24])[CH:11]=[C:15]([NH:1][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH2:4][OH:5])[C:14]1=[O:16])([CH3:20])[CH:21]([CH3:22])[CH3:23])#[N:19]

Participants

4

Reactant 2

HCID 214392-Aminobenzyl alcoholHCID 19352213HCID 19352213, compound

Product 1

HCID 13730769HCID 13730769, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To o-aminobenzyl alcohol, (2 g, 0.0125 mol) and 3-bromo-α-isopropyl-α-methyl-2,5-dioxo-3-pyrroline-1-acetonitrile (2.7 g, 0.01 mol) is added absolute ethanol (100 ml) containing 3 g of 5 A pulverized sieves. The mixture is stirred for 20 hours at room temperature. The solvent is removed and the residue is purified through a silica gel dry column, eluant ether-hexane (2:1). Starting bromomaleimide is first recovered, followed by a bright yellow solid 1.89 g (60%), mp 39°-45° C. Anal. calcd. for C17H19N3O3 : C, 65.16; H, 6.11; N, 13.41. Found: C, 65.94; H, 6.21; N, 12.87.

Workup

  1. customThe solvent is removed
  2. customthe residue is purified through a silica gel
  3. dry with materialdry column, eluant ether-hexane (2:1)
  4. customStarting bromomaleimide is first recovered

Sources & evidence

ORD record
ord-0c2209bff532473d827d5ceb079752d1
Source dataset
uspto-grants-1987_01
Patent number
US04638068

Reaction notes

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