Ethyl 4-(4-methoxybenzylamino)-6-chloropyridine-3-carboxylate → Ethyl 4-amino-6-chloronicotinate

HRID 715088Notes

Reaction equation

HRID 715088 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([NH:13]CC2C=CC(OC)=CC=2)[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1>C(O)(C(F)(F)F)=O>[NH2:13][C:11]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=[C:2]([Cl:1])[CH:12]=1

Participants

3

Reactant 1

HCID 89814202Ethyl 4-(4-methoxybenzylamino)-6-chloropyridine-3-carboxylate

Product 1

HCID 824642Ethyl 4-amino-6-chloronicotinateYield 76%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Heat a mixture of ethyl 6-chloro-4-(4-methoxybenzylamino)nicotinate (21 g, 65.6 mmol) and TFA (150 mL) at 50° C. overnight. Cool the mixture to RT, concentrate to dryness, dissolve the residue in EtOAc, wash with satd. NaHCO3 (2×), then brine (1×), dry over MgSO4, concentrate and purify via silica gel chromatography to give the title compound (10 g, 76%). 1H NMR (400 MHz, DMSO-d6): δ 8.49 (s, 1H), 7.47 (s, 2H), 6.76 (s, 1H), 4.29 (q, J=7.2 Hz, 2H), 1.31 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureHeat
  2. concentrationconcentrate to dryness
  3. dissolutiondissolve the residue in EtOAc
  4. washwash with satd
  5. dry with materialNaHCO3 (2×), then brine (1×), dry over MgSO4
  6. concentrationconcentrate
  7. custompurify via silica gel chromatography

Sources & evidence

ORD record
ord-b80b4275379c44fb86f0d138b91448f9
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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