Chloroacetyl chloride → HCID 22350167, compound
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[OH:11])[NH:7][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:5]2.[O:16]1CC[CH2:18][CH2:17]1.C(=O)([O-])O.[Na+].ClCC(Cl)=O.C(=O)([O-])[O-].[K+].[K+]>>[O:16]=[C:17]1[CH2:18][O:11][C:10]2[CH:9]=[C:8]3[NH:7][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:5][C:4]3=[CH:3][C:2]=2[NH:1]1Participants
Procedure
To a solution of 2.0 g (9.7 mmol) of methyl 5-amino-6-hydroxy-indole-2-carboxylate (Example 5/c) in 300 ml of tetrahydrofuran 2.45 g (29.2 mmol) of sodium hydrogencarbonate and 1.3 ml (16.3 mmol) of chloroacetyl chloride are added and the mixture is stirred at room temperature overnight. The reaction mixture is concentrated and 100 ml of water is added to the residue. The precipitated crystalls are filtered off, washed with water and suspended in 120 ml of acetonitrile. 4.05 g (29.3 mmol) of potassium carbonate is added to the suspension and the resulted mixture is stirred at room temperature overnight. The reaction mixture is concentrated and 100 ml of water is added to the residue. The product is filtered off, washed with water and dried to yield 1.7 g (71%) of the title compound. Mp.: 188-196° C. (water).
Workup
- concentrationThe reaction mixture is concentrated
- addition100 ml of water is added to the residue
- filtrationThe precipitated crystalls are filtered off
- washwashed with water
- stirringthe resulted mixture is stirred at room temperature overnight
- concentrationThe reaction mixture is concentrated
- addition100 ml of water is added to the residue
- filtrationThe product is filtered off
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-6a2c493bab2143ff84fd085047d857d6
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06919355B2
Reaction notes
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