Triethyl orthoacetate → 2-Methyl-1H-naphtho[2,3-d]imidazole

HRID 2231249Notes

Reaction equation

HRID 2231249 reaction equation
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[C:13](OCC)(OCC)(OCC)[CH3:14]>C(O)C.CN(C)C(=O)C>[CH3:13][C:14]1[NH:1][C:2]2[CH:3]=[C:4]3[C:9]([CH:8]=[CH:7][CH:6]=[CH:5]3)=[CH:10][C:11]=2[N:12]=1

Participants

5

Reactant 2

HCID 66221Triethyl orthoacetate2×HCID 698722,3-Diaminonaphthalene

Product 1

HCID 8398912-Methyl-1H-naphtho[2,3-d]imidazoleYield 74.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4.74 g of 2,3-diaminonaphthalene in 150 ml of ethanol and 30 ml of N,N-dimethylacetamide was added 4.86 g of triethyl orthoacetate, and the mixture heated at 60° C. for 2 hours. An additional 5.5 ml of triethyl orthoacetate was added and stirring continued at 60° C. overnight. The solvent was removed and the residue treated with chloroform. The solids were filtered and the filtrate concentrated to a small volume, treated with ether and filtered. The solids were combined to give 4.07 g of the product as a white solid.

Workup

  1. customThe solvent was removed
  2. additionthe residue treated with chloroform
  3. filtrationThe solids were filtered
  4. concentrationthe filtrate concentrated to a small volume
  5. additiontreated with ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-008b6bd36eea4de990b1ce40187f8d95
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

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