1-Nitronaphthalene → 5-Nitro-1,4,4a,9a-tetrahydroanthraquinone
Reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6](=[O:15])[CH:7]=[CH:8][C:9]2=[O:14])([O-:3])=[O:2].[CH2:16]=[CH:17][CH:18]=[CH2:19].[N+](C1C2C(=CC=CC=2)C=CC=1)([O-])=O>>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6](=[O:15])[CH:7]1[CH:8]([C:9]2=[O:14])[CH2:19][CH:18]=[CH:17][CH2:16]1)([O-:3])=[O:2]Participants
Procedure
The 5-nitro-1,4-naphthoquinone introduced into the reactor 8 for the Diels-Alder reaction is subjected to Diels-Alder reaction with 1,3-butadiene introduced from the tank 9 via a line 26 at a suitable temperature under a suitable pressure in the presence of a suitable solvent introduced from the tank 7 via a line 27. Since the unreacted 1-nitronaphthalene present in the reaction solution does not react with 1,3-butadiene, no side reaction occurs. The reaction mixture is filtered in the filter 10. The crystals of 5-nitro-1,4,4a,9a-tetrahydroanthraquinone formed by the Diels-Alder reaction are sent to the reactor 12 for the reducing reaction via a line 30, and reduced with a suitable reducing agent introduced from the tank 13 via a line 33 to form 1-aminoanthraquinone. Meanwhile, the filtrate is sent to the separation tower 11 via a line 29 and separated into the solvent and 1-nitronaphthalene by, for example, distillation. The solvent is sent to the tank 7 via a line 32, and 1-nitronaphthalene is recycled to the tank 4 via line 31 for re-use.
Workup
- additionintroduced from the tank 9 via a line 26 at a suitable temperature under a suitable pressure in the presence of a suitable solvent
- additionintroduced from the tank 7 via a line 27
- customno side reaction
- filtrationThe reaction mixture is filtered in the
- filtrationfilter 10
Sources & evidence
- ORD record
- ord-9c82340c87f349f3851965686c201593
- Source dataset
- uspto-grants-1989_06
- Patent number
- US04840749
Reaction notes
Loading…