Ammonia → Naphthalene-2-carboxamide

HRID 1020746Notes

Reaction equation

HRID 1020746 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](Cl)=[O:12].[NH3:14]>C1COCC1.C(OCC)(=O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH2:14])=[O:12]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 752462-Naphthoyl chloride

Product 1

HCID 75245Naphthalene-2-carboxamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Naphthalene-2-carbonyl chloride obtained from Step A was dissolved in THF (30 mL) and this was cooled down to 0° C. Ammonia gas was passed for approximately 1.5 hrs through the solution and the reaction was stirred at room temperature under a closed system for 4 hrs. A white solid precipitate was observed in the reaction mixture. The reaction mixture was dissolved in ethyl acetate and washed using water followed by brine solution. The organic layer was separated and dried over sodium sulphate and the volatiles were evaporated off in vacuo to afford the crude product.

Workup

  1. washwashed
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulphate
  4. customthe volatiles were evaporated off in vacuo

Sources & evidence

ORD record
ord-4dde2515992342ec845ce8ad7ff7f133
Source dataset
uspto-grants-2014_05
Patent number
US08716473B2

Reaction notes

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