1,4-Naphthoquinone → Mitoquidone

HRID 1762110Notes

Reaction equation

HRID 1762110 reaction equation
[CH:1]([N:3]1[CH:12]([C:13](O)=O)[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1)=O.[C:16]1(=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](=[O:26])[CH:18]=C1>C(OC(=O)C)(=O)C>[CH:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH2:11][C:12]1[N:3]([CH:1]=[C:18]3[C:13]=1[C:16](=[O:27])[C:25]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:19]3=[O:26])[CH2:4]2

Participants

4

Reactant 2

HCID 85301,4-NaphthoquinoneHCID 123241712-Formyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 71772Mitoquidone

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-formyl-3-carboxy-1,2,3,4-tetrahydroisoquinoline (20 g) and 1,4-naphthoquinone (30.8 g) in acetic anhydride (500 ml) was heated at 100° C. with stirring for 30 minutes. The reaction mixture was cooled, the solid collected by filtration, washed with acetic anhydride (50 g) with ether (2×100ml) and dried to give the title compound in Form B (26 g).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe solid collected by filtration
  3. washwashed with acetic anhydride (50 g) with ether (2×100ml)
  4. customdried

Sources & evidence

ORD record
ord-3e6c57dee69d483db1b29de38c740d3c
Source dataset
uspto-grants-1989_05
Patent number
US04831039

Reaction notes

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