Hydroxyamine hydrochloride → HCID 73665311, compound

HRID 652241Notes

Reaction equation

HRID 652241 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][N:7]3[C:12](=O)[CH2:13][CH2:14][CH:6]3[C:5](=[O:16])[C:4]=2[CH:3]=1.[OH2:17].O.O.C([O-])(=O)C.[Na+].Cl.[NH2:26]O>C(O)C.O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][N:7]3[CH2:12][CH2:13][C:14](=[N:26][OH:17])[CH:6]3[C:5](=[O:16])[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 131500848-Chloro-1,10a-dihydropyrrolo[1,2-b]isoquinoline-3,10(2H,5H)-dioneHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 73665311HCID 73665311, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A stirred suspension of 12.65 g of 8-chloro-1,10a-dihydropyrrolo[1,2-b]isoquinoline-3,10[2H,5H]-dione (prepared in substantially the same manner as the 7-chloro compound in Example 12, m.p. 130°-136° C.) in 95% ethanol (85 ml) was treated with a premixed solution prepared from sodium acetate trihydrate (14.56 g) in water (48 ml) and hydroxylamine hydrochloride (7.44 g) in water (48 ml). The stirred suspension was heated to reflux, during which a solution formed followed by separation of a crystalline precipitate. After 2 hours of refluxing, the mixture was cooled and the precipitate was collected and washed twice with 50% aqueous ethanol. Drying at 40° C. overnight in vacuo gave 10.95 g of a solid, m.p. 227.5°-230.5° C. Recrystallization of the solid from n-propanol (300 ml) afforded 8.56 g of crystals, m.p. 229°-235° C.

Workup

  1. additionwas treated with a premixed solution
  2. temperatureThe stirred suspension was heated
  3. temperatureto reflux, during which a solution
  4. customformed
  5. customfollowed by separation of a crystalline precipitate
  6. temperatureAfter 2 hours of refluxing
  7. temperaturethe mixture was cooled
  8. customthe precipitate was collected
  9. washwashed twice with 50% aqueous ethanol
  10. customDrying at 40° C. overnight in vacuo

Sources & evidence

ORD record
ord-9561b31e986b4d658f293fb7552cc84c
Source dataset
uspto-grants-1987_06
Patent number
US04670562

Reaction notes

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