Acetic Anhydride → Benafentrine

HRID 1659196Notes

Reaction equation

HRID 1659196 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[CH:18]=[C:19]([O:24][CH3:25])[C:20]([O:22][CH3:23])=[CH:21][C:16]=3[C@H:15]3[C@H:10]([CH2:11][CH2:12][N:13]([CH3:26])[CH2:14]3)[N:9]=2)=[CH:4][CH:3]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>N1C=CC=CC=1>[C:27]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[CH:18]=[C:19]([O:24][CH3:25])[C:20]([O:22][CH3:23])=[CH:21][C:16]=3[C@H:15]3[C@H:10]([CH2:11][CH2:12][N:13]([CH3:26])[CH2:14]3)[N:9]=2)=[CH:4][CH:3]=1)(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86733645HCID 86733645, compound

Product 1

HCID 3084603Benafentrine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.0 g of cis-6-(4-aminophenyl)-1,2,3,4,4a,10b-hexahydro-8,9-dimethoxy-2-methyl-benzo[c][1,6]naphthyridine (produced as in Example 5) is heated to 60° in a mixture of 2 cc of pyridine and 2 cc of acetic anhydride for 2 hours. The reaction mixture is then evaporated to dryness in a vacuum and the residue is crystallized from acetone. M.P. 173°-175°.

Workup

  1. customThe reaction mixture is then evaporated to dryness in a vacuum
  2. customthe residue is crystallized from acetone

Sources & evidence

ORD record
ord-8c740cdc30ba4804a2cf37abeb9dbb7d
Source dataset
uspto-grants-1976_06
Patent number
US03966938

Reaction notes

Loading…