Water → 2-Amino-6-methoxybenzonitrile

HRID 1169987Notes

Reaction equation

HRID 1169987 reaction equation
F[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=CC(=O)[NH:9]2)=[CH:4][CH:3]=1.CN.O.C[CH2:17][OH:18].C[N:20]1C(=O)CCC1>>[NH2:9][C:10]1[CH:11]=[CH:2][CH:3]=[C:4]([O:18][CH3:17])[C:5]=1[C:6]#[N:20]

Participants

5

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 18313719HCID 18313719, compoundHCID 190675757-Fluoroquinolin-2(1H)-one

Product 1

HCID 127157142-Amino-6-methoxybenzonitrile

Procedure

A 7-Fluoroquinolinone derivative in a 8 M solution of MeNH2 in EtOH:NMP (1:1), was submitted to microwave irradiation 4 times for 5 minutes at 220° C. After cooling, water was added, and the mixture was extracted with EtOAc. The organic extracts were collected and dried over Na2SO4. Evaporation of the solvent under reduced pressure and purification of the residue by reverse phase preparative HPLC afforded the desired product. Other primary and secondary amines were used neat, 1:1 with NMP.

Workup

  1. customirradiation 4 times for 5 minutes at 220° C
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with EtOAc
  4. customThe organic extracts were collected
  5. dry with materialdried over Na2SO4
  6. customEvaporation of the solvent
  7. customunder reduced pressure and purification of the residue by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-3042359669ab4ca9b379ef5b7934753a
Source dataset
uspto-grants-2010_11
Patent number
US07825132B2

Reaction notes

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