Water → HCID 15125647, compound

HRID 2107790Notes

Reaction equation

HRID 2107790 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([OH:14])[C:6](=[CH:11][C:12]=1[Cl:13])[C:7]([O:9][CH3:10])=[O:8].[C:15](Cl)(=[O:17])[CH3:16].O.[CH2:20]([O:22]C(=O)C)[CH3:21].CCCCCC>N1C=CC=CC=1.C(Cl)Cl>[C:15]([O:14][C:5]1[CH:4]=[C:3]([NH:2][C:20](=[O:22])[CH3:21])[C:12]([Cl:13])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:17])[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 21226206Ethyl acetate hexaneHCID 23046753HCID 23046753, compound

Product 1

HCID 15125647HCID 15125647, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 10.9 g (54 mmol) of methyl 4-amino-5-chlorosalicylate hydrochloride diluted with 250 ml pyridine is stirred at 0° C. and treated with 17 g (0.22 mol, 16 mls) of acetyl chloride over a 10 minute period. A ppt. begins to form and the mixture is stirred 30 minutes longer at 0° C. This is then treated with 30 ml H2O and stirred for 5 minutes after which time the ppt. dissolves. The mixture is diluted with CH2Cl2 (500 ml), washed with H2O (500 ml) and 10% HCl (4×300 ml). The organic layer is dried (MgSO4) and evaporated to dryness to obtain crude product which is recrystallyzed from ethylacetate-hexane to obtain pure methyl 2-acetoxy-4-acetylamino-5-chlorobenzoate; m.p. 134°-36° C.

Workup

  1. customto form
  2. stirringthe mixture is stirred 30 minutes longer at 0° C
  3. stirringstirred for 5 minutes after which time the ppt
  4. dissolutiondissolves
  5. washwashed with H2O (500 ml) and 10% HCl (4×300 ml)
  6. dry with materialThe organic layer is dried (MgSO4)
  7. customevaporated to dryness
  8. customto obtain crude product which

Sources & evidence

ORD record
ord-36976d2b669948c984fa86265913252c
Source dataset
uspto-grants-1990_06
Patent number
US04935511

Reaction notes

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