Hydrochloric Acid → HCID 12504729, compound

HRID 1904394Notes

Reaction equation

HRID 1904394 reaction equation
O.NN.[C:4]([NH:7][C:8]1[CH:29]=[CH:28][C:11]([O:12][CH2:13][CH:14]([OH:27])[CH2:15][N:16]2C(=O)C3=CC=CC=C3C2=O)=[CH:10][CH:9]=1)(=[O:6])[CH3:5].[ClH:30]>C(O)C>[ClH:30].[NH2:16][CH2:15][CH:14]([OH:27])[CH2:13][O:12][C:11]1[CH:28]=[CH:29][C:8]([NH:7][C:4](=[O:6])[CH3:5])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 13934174HCID 13934174, compound

Product 1

HCID 12504729HCID 12504729, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Hydrazine hydrate (3.6 g, 0.071 mol) was dissolved in 50 ml ethanol and added slowly to a suspension of Compound XVII (25 g, 0.071 mol) in 300 ml boiling ethanol. After 30 min., all the material dissolved. The temperature of the reaction mixture was reduced to 75° C. and maintained for an additional 1.5 hr. At the end of this time, the mixture was cooled to room temperature and concentrated hydrochloric acid added dropwise to pH 1 (pH paper) to destroy the hydrazide intermediate. Since not all of the material dissolved, the mixture was filtered to remove undissolved phthalhydrazide and the filtrate stored at 4° C. overnight. Filtration of the newly precipitated material gave 10.6 g of the title compound m.p. 192°-197° C. Recrystallization from ethanol/ether yielded 9.0 g of small white cluster crystals which were homogenous by thin layer chromatography (30:10:3:12 butanol/pyridine/acetic acid/water, Rf =0.46) m.p. 198.5°-200° C.

Workup

  1. dissolutionall the material dissolved
  2. customwas reduced to 75° C.
  3. temperaturemaintained for an additional 1.5 hr
  4. customto destroy the hydrazide intermediate
  5. dissolutionSince not all of the material dissolved
  6. filtrationthe mixture was filtered
  7. customto remove undissolved phthalhydrazide
  8. waitthe filtrate stored at 4° C. overnight
  9. filtrationFiltration of the newly precipitated material

Sources & evidence

ORD record
ord-9069567367544cde89bfb218c977496b
Source dataset
uspto-grants-1989_06
Patent number
US04837305

Reaction notes

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