N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)acetamide → Ammonia

HRID 22105Notes

Reaction equation

HRID 22105 reaction equation
[CH3:1][C:2]([NH:4][CH:5]1[C:21]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[C:18]([CH:20]=2)=[O:19])[C:13]2[C:8](=[CH:9][C:10]([O:28][CH3:29])=[C:11]([O:26][CH3:27])[C:12]=2[O:24][CH3:25])[CH2:7][CH2:6]1)=[O:3].CC([NH:33][C@@H]1C2C(=CC=C(OC)C(C=2)=O)C2C(OC)=C(OC)C(OC)=CC=2CC1)=O.CSC.[Na].CC(CC(C1C(O)=CC(O)=C(CC=C(C)C)C=1[O-])=O)C.[O-]CC.[Na+]>CO>[CH3:1][C:2]([NH:4][C@@H:5]1[C:21]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[C:18]([CH:20]=2)=[O:19])[C:13]2[C:12]([O:24][CH3:25])=[C:11]([O:26][CH3:27])[C:10]([O:28][CH3:29])=[CH:9][C:8]=2[CH2:7][CH2:6]1)=[O:3].[NH3:33]

Participants

8

Reactant 5

HCID 2833N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)acetamideHCID 6167Colchicine3×HCID 2723922Sodium ethoxideHCID 252006104-PrenylphlorisovalerophenoneHCID 86593196Sodium methylsulfide

Product 2

HCID 222AmmoniaHCID 6167Colchicine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

FIG. 6 illustrates how alternative colchine derivatives were prepared. For example, thiocholcine (compound IX) was prepared by reacting colchicine with sodium methyl sulfide (Velluz). Another colchicine derivative, 10-demethoxy-10-ethoxycolchicine (compound X) can be prepared by reacting colchicine with sodium ethoxide to generate 10-demethoxy-10-ethoxycolchicine. Colchicinamide (compound XI) can be formed by reaction of colchicine with ammonia in methanol (Lettre). Colchicinamide can be further reacted with ethyliodide to generate 10-demethoxy-10-ethylaminocolchicine (compound XII) (Bishop). Alternatively, 10-demethoxy-10-ethylaminocolchicine (compound XII) can be prepared directly from colchicine by reaction with ethylamine (Lettre).

Workup

  1. customwere prepared

Sources & evidence

ORD record
ord-20462acb03f44b94af918c2c8fa90cf5
Source dataset
uspto-grants-1995_06
Patent number
US05426224

Reaction notes

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