Hydrochloric Acid → HCID 13851335, compound

HRID 979167Notes

Reaction equation

HRID 979167 reaction equation
[Br:1][C:2]1[C:7]2[O:8][CH2:9][C@@H:10]3[C@@H:15]([CH2:16][N:17]4C(=O)C5=CC=CC=C5C4=O)[CH2:14][N:13]([CH3:28])[CH2:12][C@H:11]3[C:6]=2[CH:5]=[C:4]([O:29][CH3:30])[CH:3]=1.O.NN.Cl>CO>[NH2:17][CH2:16][C@@H:15]1[CH2:14][N:13]([CH3:28])[CH2:12][C@H:11]2[C:6]3[CH:5]=[C:4]([O:29][CH3:30])[CH:3]=[C:2]([Br:1])[C:7]=3[O:8][CH2:9][C@H:10]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 13851333HCID 13851333, compound

Product 1

HCID 13851335HCID 13851335, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To suspension of 0.305 g (±)-[4R*,4aS*,10bR*]-7-bromo-1,3,4,4a,5,10b-hexahydro-9-methoxy-2-methyl-4-(phthalimidomethyl)-2H-[1]benzopyrano[4,3-c]pyridine in 40 ml MeOH, is added 0.102 ml hydrazine hydrate. The mixture is refluxed 12 hours, cooled, acidified to pH 1 with 12N HCl, and concentrated to a 3 ml volume under reduced pressure. The residue is partitioned between 10 ml 2N NaOH and CH2Cl2 (40 ml). The organic phase is dried over MgSO4, filtered, and evaporated to dryness in vacuo to yield the title compound; m.p. HCl salt 277°-279° dec.

Workup

  1. temperatureThe mixture is refluxed 12 hours
  2. temperaturecooled
  3. concentrationconcentrated to a 3 ml volume under reduced pressure
  4. customThe residue is partitioned between 10 ml 2N NaOH and CH2Cl2 (40 ml)
  5. dry with materialThe organic phase is dried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-2d61113017f84c48a32856afc6c6c7df
Source dataset
uspto-grants-1987_05
Patent number
US04666916

Reaction notes

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