Water → Emakalim

HRID 1974834Notes

Reaction equation

HRID 1974834 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8]([CH3:14])([CH3:13])[CH:7]1[O:15][CH:6]21)#[N:2].[OH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1.O>O1CCOCC1>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8]([CH3:14])([CH3:13])[C@@H:7]([OH:15])[C@@H:6]2[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]1=[O:16])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 66854Benzyltrimethylammonium hydroxideHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochromanHCID 178516071HCID 178516071, compound

Product 1

HCID 9839143Emakalim

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1 g of 6-cyano-2,2-dimethyl-3,4-epoxychromane is refluxed for 40 hours with I g of 2-hydroxypyridine in 10 ml of dioxane, in the presence of 0.20 ml of a methanolic solution containing 35% of benzyltrimethylammonium hydroxide. The mixture is taken up with 30 ml of water and the precipitate obtained is-filtered off, washed with isopropyl ether and then recrystallized from 20 ml of absolute ethyl alcohol to give 0.9 g of the expected product.

Workup

  1. customthe precipitate obtained
  2. filtrationis-filtered off
  3. washwashed with isopropyl ether
  4. customrecrystallized from 20 ml of absolute ethyl alcohol

Sources & evidence

ORD record
ord-bff3a2ecebb34b5e80e188233d4eb4c7
Source dataset
uspto-grants-1994_02
Patent number
US05284838

Reaction notes

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