Benzyltrimethylammonium hydroxide → trans-6-Cyano-4-(1,6-dihydro-6-oxopyridazin-1-yl)-2,2-dimethylchroman-3-ol

HRID 1974837Notes

Reaction equation

HRID 1974837 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[N:18]=[N:19][CH:20]=[CH:21][CH:22]=1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>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[C:17](=[O:16])[CH:22]=[CH:21][CH:20]=[N:19]1)#[N:2]

Participants

5

Reactant 3

HCID 66854Benzyltrimethylammonium hydroxideHCID 681533(2H)-PyridazinoneHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochroman

Product 1

HCID 14182615trans-6-Cyano-4-(1,6-dihydro-6-oxopyridazin-1-yl)-2,2-dimethylchroman-3-olYield 60.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1 g of 6-cyano-2,2-dimethyl-3,4-epoxychromane and 1 g of 3-hydroxypyridazine are refluxed for 20 hours in 5 ml of dioxane, in the presence of 0.20 ml of a methanolic solution containing 35% of benzyltrimethylammonium hydroxide. The mixture is concentrated under vacuum and the residue is then triturated in 20 ml of water; the precipitate obtained is filtered off, washed with water and isopropyl ether and then recrystallized from 10 ml of isopropyl alcohol to give 0.9 g of the expected product.

Workup

  1. concentrationThe mixture is concentrated under vacuum
  2. customthe residue is then triturated in 20 ml of water
  3. customthe precipitate obtained
  4. filtrationis filtered off
  5. washwashed with water and isopropyl ether
  6. customrecrystallized from 10 ml of isopropyl alcohol

Sources & evidence

ORD record
ord-4f453709b7d440009d32f788c4041716
Source dataset
uspto-grants-1994_02
Patent number
US05284838

Reaction notes

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