Formamide → 4-AMINO-3-CHLOROBENZAMIDE

HRID 1157400Notes

Reaction equation

HRID 1157400 reaction equation
C[N:2]([CH:4]=[O:5])C.[NH2:6][C:7]1[CH:16]=[CH:15][C:10](C(OC)=O)=[CH:9][C:8]=1[Cl:17].C(N)=O.C[O-].[Na+]>CC(O)C>[NH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:4]([NH2:2])=[O:5])=[CH:9][C:8]=1[Cl:17]

Participants

6

Reactant 4

HCID 713FormamideHCID 6228DimethylformamideHCID 1515284Methyl 4-Amino-3-chlorobenzoateHCID 10942334Sodium Methoxide

Product 1

HCID 121180544-AMINO-3-CHLOROBENZAMIDE

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

An anhydrous DMF solution of 1.00 g (5.39 mmol) of methyl 4-amino-3-chlorobenzoate (17-1), 728 mg (16.16 mmol) of formamide and 204 mg (3.77 mmol) of 5.5M sodium methoxide was stirred for 1 hour at 100° C. and then stirred overnight at room temperature. The reaction was poured into 2-propanol (60 mL) and then evaporated off the solvent. The resultant crude oil was purified on a silica column and eluted with DCM:MeOH:NH4OH (95:5:0.5 to 9:1:0.1). Recovered the desired product 17-2. MS (M+1): measured 171.2; theoretical 170.0. 1H NMR (DMSO): 5.86 (s, 2H), 6.75 (d, 1H), 7.01 (bs, 1H), 7.56 (dd, 1H), 7.66 (bs, 1H), 7.75 (m, 1H).

Workup

  1. customevaporated off the solvent
  2. customThe resultant crude oil was purified on a silica column
  3. washeluted with DCM:MeOH:NH4OH (95:5:0.5 to 9:1:0.1)
  4. customRecovered the desired product 17-2

Sources & evidence

ORD record
ord-20928f744ddd48328a950293d5652072
Source dataset
uspto-grants-2010_10
Patent number
US07807684B2

Reaction notes

Loading…