Hydrochloric Acid → HCID 10106332, compound

HRID 1684102Notes

Reaction equation

HRID 1684102 reaction equation
[C:1]([C:4]1[C:5]([N+:20]([O-])=O)=[C:6]([O:18][CH3:19])[C:7]([C:15](=[O:17])[NH2:16])=[C:8]([N+:12]([O-])=O)[C:9]=1[O:10][CH3:11])(=[O:3])[NH2:2].CO.Cl>[Pd].C(O)CCC.C(O)(=O)C.O>[C:15]([C:7]1[C:8]([NH2:12])=[C:9]([O:10][CH3:11])[C:4]([C:1](=[O:3])[NH2:2])=[C:5]([NH2:20])[C:6]=1[O:18][CH3:19])(=[O:17])[NH2:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 9972908HCID 9972908, compound

Product 1

HCID 10106332HCID 10106332, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22056973Butanol acetic acid waterSolvent

Procedure

A mixture consisting of 561 mg (1.79 mmol) of 6, 50 mg of 5% Pd/C, and 100 mL of methanol was shaken under 50 psi of H2 for 4 hours. Upon completing the reduction, 10 mL of concentrated hydrochloric acid was added immediately to the reaction mixture with stirring. After filtering the acidified mixture through CELITE and washing with methanol, the solvents were evaporated in vacuo and the solid residue thoroughly dried. The 8·2HCl was purified by dissolution in a minimum amount of hot methanol followed by addition of ethyl acetate: 568 mg (97%) yield; TLC (n-butanol/acetic acid/water [5:2:3]), Rf =0.37; 1H NMR (dimethyl-d6 sulfoxide) δ7.93 and 7.92 (4H, 2 brs, 3- and 6-carbamyls, no assignments made), 3.69 (6H, s, methoxys); mass spectrum (EI mode), m/z 254 (P+).

Workup

  1. additionwas added immediately to the reaction mixture
  2. stirringwith stirring
  3. filtrationAfter filtering the acidified mixture through CELITE
  4. washwashing with methanol
  5. customthe solvents were evaporated in vacuo
  6. customthe solid residue thoroughly dried
  7. customThe 8·2HCl was purified by dissolution in a minimum amount of hot methanol
  8. additionfollowed by addition of ethyl acetate
  9. custom568 mg (97%) yield

Sources & evidence

ORD record
ord-0ce12021a1e543cd8ca80c1b9c5a81c1
Source dataset
uspto-grants-1997_06
Patent number
US05639881

Reaction notes

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