Ethyl orthoformate → HCID 9972639, compound

HRID 1672320Notes

Reaction equation

HRID 1672320 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[CH:11][C:10]=1[NH2:21].[CH2:22](OC(OCC)OCC)C>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:9]2[C:18]3[CH:17]=[C:16]([O:19][CH3:20])[CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:21]=[CH:22]1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 60046938HCID 60046938, compound

Product 1

HCID 9972639HCID 9972639, compound

Procedure

0.2 g (0.66 mmol) of N4-(2-chloro-phenyl)-6-methoxy-quinoline-3,4-diamine (Example 44i) in 6 ml triethylorthoformate are heated under reflux for 4 h. The solvent is evaporated almost to dryness, the dark residue is dissolved in ca. 1 ml ethyl acetate and the compound is precipitated by adding ca. 30 ml of hexane. The desired title compound is filtered off, and is dried for 16 h at 60° C. (high-vacuum). mp: 202-205° C.; MS: 310 (M++1); HPLC: tret=70.56 min (Grad 1).

Workup

  1. temperatureunder reflux for 4 h
  2. customThe solvent is evaporated almost to dryness
  3. dissolutionthe dark residue is dissolved in ca. 1 ml ethyl acetate
  4. customthe compound is precipitated
  5. additionby adding ca. 30 ml of hexane
  6. filtrationThe desired title compound is filtered off
  7. customis dried for 16 h at 60° C. (high-vacuum)
  8. customtret=70.56 min (Grad 1)

Sources & evidence

ORD record
ord-3f88c14a28634f929db3946ebe500e95
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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