HCID 67255662, compound → HCID 67254134, compound

HRID 1821766Notes

Reaction equation

HRID 1821766 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH:13]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=2[NH:30]C(OC(C)(C)C)=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl.O1CCOCC1>[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH:13]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=2[NH2:30])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 67255662HCID 67255662, compound

Product 1

HCID 67254134HCID 67254134, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of the crude 3-(2-tert-Butoxycarbonylamino-4-methyl-phenoxymethyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester (crude, 0.35 mmol) in 4N HCl in dioxane (2 mL) at room temperature was stirred under a drying tube overnight. The suspension was concentrated by rotovap, diluted to 30 mL with CH2Cl2 and shaken with 10% Na2CO3 (30 mL). The organics were isolated, dried (MgSO4), filtered and concentrated to a brown oil corresponding to the crude aniline, which was used without purification in the urea forming reaction.

Workup

  1. concentrationThe suspension was concentrated by rotovap
  2. additiondiluted to 30 mL with CH2Cl2
  3. customThe organics were isolated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a brown oil corresponding to the crude aniline, which
  7. customwas used without purification in the urea forming reaction

Sources & evidence

ORD record
ord-e5435df3af354fcda76c9f7fa60fc652
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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