Amsacrine → m-AMSA D-galacturonate

HRID 434773Notes

Reaction equation

HRID 434773 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=2[N:17]=[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=12.O.[O:30]=[CH:31][C@@H:32]([C@H:34]([C@H:36]([C@@H:38]([C:40]([OH:42])=[O:41])[OH:39])[OH:37])[OH:35])[OH:33]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=12.[O:30]=[CH:31][C@@H:32]([C@H:34]([C@H:36]([C@@H:38]([C:40]([O-:42])=[O:41])[OH:39])[OH:37])[OH:35])[OH:33]

Participants

4

Reactant 2

HCID 2179AmsacrineHCID 44654794D-Galacturonic acid monohydrate

Product 1

HCID 86738978m-AMSA D-galacturonateYield 66.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.93 gm of m-AMSA and 2.12 gm of D-galacturonic acid monohydrate in 325 ml of specially denatured 3A anhydrous ethanol at 70°-80° C. is filtered with suction. The filtrate is stirred and chilled to 0°-5° C., then stored at -20° C. for about 16 hours. The product is collected, washed with cold (about -20° C.) specially denatured 3A anhydrous ethanol, then with anhydrous diethyl ether and dried under reduced pressure at 50°-55° C. to give 3.9 gm of m-AMSA D-galacturonate. The salt obtained by this process retains a small amount about 3% of ethanol.

Workup

  1. customat 70°-80° C.
  2. filtrationis filtered with suction
  3. temperaturechilled to 0°-5° C.
  4. customThe product is collected
  5. washwashed with cold (about -20° C.)
  6. dry with materialwith anhydrous diethyl ether and dried under reduced pressure at 50°-55° C.

Sources & evidence

ORD record
ord-3b53ae40001a4b5694f2e21fe98ebb22
Source dataset
uspto-grants-1983_08
Patent number
US04399283

Reaction notes

Loading…