Sodium Acetate → HCID 19076181, compound

HRID 965279Notes

Reaction equation

HRID 965279 reaction equation
[Cl:1][C:2]1(Cl)[CH2:8][CH2:7][C:6]2[CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:17].ClN1C2C=CC(C(OC)=O)=CC=2CCC(Cl)(Cl)C1=O.CC([O-])=O.[Na+]>[Pd].C(O)(=O)C>[Cl:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:17]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 19076174HCID 19076174, compoundHCID 19076187HCID 19076187, compound

Product 1

HCID 19076181HCID 19076181, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A 10% Pd/C mixture (0.9 g) was added to a mixture of 3,3-dichloro-7-carbomethoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one 3 and 1,3,3-trichloro-7-carbomethoxy-2,3,4,5-tetrahydro-1-benzazepin-2-one (9.34 g), NaOAc (5.51 g, 40.5 mmol), and glacial acetic acid (25 mL). After stirring under a hydrogen atmosphere (balloon) at RT for 3.5 h and at 60° C. for an additional 30 min, the reaction mixture was filtered (celite) and concentrated. The resulting material was partitioned between saturated NaHSO4 (aqueous) and CH2Cl2. The organic layer was removed and the aqueous layer was extracted with CH2Cl2 (×2). The combined organic extracts were dried (Na2SO4) and concentrated to give 4 (3.6 g). LRMS (ES), [M+H] m/z=254.

Workup

  1. waitat 60° C. for an additional 30 min
  2. filtrationthe reaction mixture was filtered (celite)
  3. concentrationconcentrated
  4. customThe resulting material was partitioned between saturated NaHSO4 (aqueous) and CH2Cl2
  5. customThe organic layer was removed
  6. extractionthe aqueous layer was extracted with CH2Cl2 (×2)
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7a35e00401954a0da40f9fabf967ec7e
Source dataset
uspto-grants-1998_06
Patent number
US05773512

Reaction notes

Loading…