2-Naphthylamine → 1H-Benz(e)indole-1,2(3H)-dione

HRID 1725871Notes

Reaction equation

HRID 1725871 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[NH2:11].[O:12]=[C:13](C(OCC)=O)[C:14](OCC)=[O:15].[OH-].[K+]>C(O)(=O)C.O>[C:14]1(=[O:15])[C:1]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[CH:4]=[CH:3][C:2]=2[NH:11][C:13]1=[O:12]

Participants

6

Reactant 3

HCID 70572-NaphthylamineHCID 14797Potassium HydroxideHCID 691051,3-Diethyl 2-oxopropanedioate

Product 1

HCID 2000871H-Benz(e)indole-1,2(3H)-dioneYield 79.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-naphthylamine (8.0 g, 56 mmol) in glacial acetic acid (500 mL) was treated with diethyl ketomalonate (9.2 mL, 62 mmol), heated to 120° C. for 4 hours, and concentrated. The concentrate was suspended in a solution of KOH (36.8 g, 690 mmol) in water (736 mL) and stirred overnight with a stream of air blowing into the solution. The resulting mixture was filtered and the filtrate was adjusted to approximately pH 3 with concentrated HCl. The resulting suspension was cooled to 0° C. and filtered. The filter cake was dried under vacuum to provide the desired product (8.76 g, 79%). MS (DCI) m/e 198 (M+H)+, 215 (M+NH4)+.

Workup

  1. concentrationconcentrated
  2. filtrationThe resulting mixture was filtered
  3. temperatureThe resulting suspension was cooled to 0° C.
  4. filtrationfiltered
  5. customThe filter cake was dried under vacuum

Sources & evidence

ORD record
ord-e3ca3f1cb58f4de5b90d6118453fa4c8
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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