HCID 13102478, compound → HCID 13102479, compound

HRID 1758541Notes

Reaction equation

HRID 1758541 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]([N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17][CH:16]1[C:25]([OH:27])=[O:26])=[O:14]>CO.O.C(O)C.O>[NH2:3][CH2:12][C:13]([N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17][CH:16]1[C:25]([OH:27])=[O:26])=[O:14]

Participants

5

Reactant 1

HCID 13102478HCID 13102478, compound

Product 1

HCID 13102479HCID 13102479, compoundYield 38.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

To a stirred mixture of the compound of Example I (75.2 g, 0.206 mole) and methanol (400 ml) was added 85% N2H4.H2O (12.7 ml, 0.220 mole) dissolved in methanol (30 ml) dropwise over 0.5 hours. After stirring under ambient conditions for 15 minutes, the solution was heated to reflux. Reflux was maintained for 6.0 hours, then allowed to cool overnight at 0°. The crystalline solid was collected, washed with methanol (50 ml) and air dried to give 68.0 g. This solid (68.0 g) was stirred in H2O (175 ml) for 2.0 hours, then filtered. The insoluble solid was washed with H2O (2×5 ml). The filtrate and washing were combined and concentrated under high vacuum to 1/3 its volume. This was diluted with abs. ethanol (150 ml) and concentrated under reduced pressure to a solid residue. This residue was triturated in abs. ethanol (100 ml), collected by filtration and air dried to give 25.2 g. This crude solid was stirred in ethanol/H2O (9:1, 300 ml) for 2.0 hours, filtered and air dried to give 18.6 g (0.079 mole, 38% yield) of title product.

Workup

  1. temperaturethe solution was heated to reflux
  2. temperatureReflux
  3. temperaturewas maintained for 6.0 hours
  4. temperatureto cool overnight at 0°
  5. customThe crystalline solid was collected
  6. washwashed with methanol (50 ml) and air
  7. customdried
  8. customto give 68.0 g
  9. filtrationfiltered
  10. washThe insoluble solid was washed with H2O (2×5 ml)
  11. washThe filtrate and washing
  12. concentrationconcentrated under high vacuum to 1/3 its volume
  13. additionThis was diluted with abs
  14. concentrationethanol (150 ml) and concentrated under reduced pressure to a solid residue
  15. customThis residue was triturated in abs
  16. filtrationethanol (100 ml), collected by filtration and air
  17. customdried
  18. customto give 25.2 g
  19. filtrationfiltered
  20. customair dried

Sources & evidence

ORD record
ord-f9f88619b4c449d5a7f61fe32874c550
Source dataset
uspto-grants-1983_02
Patent number
US04374246

Reaction notes

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