HCID 54086598, compound → HCID 9954184, compound

HRID 2108048Notes

Reaction equation

HRID 2108048 reaction equation
C([O:4][CH:5]([CH2:15][N:16](C(=O)C)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([NH2:13])=[C:8]([Cl:14])[CH:7]=1)(=O)C>[OH-].[Na+].C(O)C>[NH2:13][C:9]1[C:10]([Cl:12])=[CH:11][C:6]([CH:5]([CH2:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[OH:4])=[CH:7][C:8]=1[Cl:14]

Participants

4

Reactant 1

HCID 54086598HCID 54086598, compound

Product 1

HCID 9954184HCID 9954184, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of α-[[acetyl[6-[2-(2-pyridinyl)ethoxy]hexyl]amino]methyl]-4-amino-3,5-dichlorobenzenemethanol acetate (ester) (130 mg) in sodium hydroxide (5 ml) and ethanol (5 ml) was stirred at room temperature for 18 h. The mixture was heated under reflux for 20 h, cooled, evaporated in vacuo and the aqueous layer extracted with ethyl acetate (2×20 ml). The combined organic extracts were dried and concentrated to give a yellow oil which was triturated in ether/hexane to give the title compound as a white solid (80 mg) m.p. 92°-95°, t.l.c. (System A 80:20:1) Rf 0.44.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 20 h
  3. temperaturecooled
  4. customevaporated in vacuo
  5. extractionthe aqueous layer extracted with ethyl acetate (2×20 ml)
  6. customThe combined organic extracts were dried
  7. concentrationconcentrated
  8. customto give a yellow oil which
  9. customwas triturated in ether/hexane

Sources & evidence

ORD record
ord-f2e8299986804b618fdd12e1f5ba36be
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

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