1,2-Naphthalenediamine → HCID 178432073, compound

HRID 2231250Notes

Reaction equation

HRID 2231250 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH2:12].[C:13](OCC)(OCC)(OCC)[CH3:14]>C(O)C>[CH3:13][C:14]1[NH:1][C:2]2[C:11]3[C:6]([CH:5]=[CH:4][C:3]=2[N:12]=1)=[CH:7][CH:8]=[CH:9][CH:10]=3

Participants

4

Reactant 2

HCID 136481,2-NaphthalenediamineHCID 66221Triethyl orthoacetate

Product 1

HCID 178432073HCID 178432073, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7.38 g of 1,2-diaminonaphthalene in 175 ml of ethanol was added 8.56 ml of triethyl orthoacetate and the reaction mixture heated to reflux for 3.5 hours. The solvent was removed in vacuo and the residue partitioned between chloroform and water. The organic phase was separated, dried over magnesium sulfate and concentrated to a dark oil, 9.0 g.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 3.5 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue partitioned between chloroform and water
  5. customThe organic phase was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to a dark oil, 9.0 g

Sources & evidence

ORD record
ord-6865c7ab614b466c9be70ca655209577
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

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