Hydrochloric Acid → (5,6-Dihydroxy-7-nitro-1-benzothiophen-2-yl)(morpholin-4-yl)methanone

HRID 1881182Notes

Reaction equation

HRID 1881182 reaction equation
[OH:1][C:2]1[C:3]([O:22]C)=[CH:4][C:5]2[CH:9]=[C:8]([C:10]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[O:11])[S:7][C:6]=2[C:18]=1[N+:19]([O-:21])=[O:20].N1C=CC=CC=1.[Cl-].[Cl-].[Cl-].[Al+3].Cl>C(OCC)(=O)C>[OH:22][C:3]1[C:2]([OH:1])=[C:18]([N+:19]([O-:21])=[O:20])[C:6]2[S:7][C:8]([C:10]([N:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)=[O:11])=[CH:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6451240Aluminum(III) ChlorideHCID 67094194HCID 67094194, compound

Product 1

HCID 15983103(5,6-Dihydroxy-7-nitro-1-benzothiophen-2-yl)(morpholin-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

(6-Hydroxy-5-methoxy-7-nitro-benzo[b]thiophen-2-yl)-morpholin-4-yl-methanone (1.0 g) was dissolved in ethyl acetate (11 ml) and pyridine (14 ml) added into. Next aluminum trichloride (0.47 g) was gradually added into the solution. The reaction mixture was refluxed for 2 hours at 110° C. To the warm reaction (60° C.) solution was added the mixture of ice and concentrated hydrochloric acid (1:1) and then it was stirred at room temperature for one hour. The solid was filtered, washed with water and treated with diethyl ether.

Workup

  1. customTo the warm reaction (60° C.) solution
  2. additionwas added
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. additiontreated with diethyl ether

Sources & evidence

ORD record
ord-ee18e3cf93df4d7fb112beaec2a6b97f
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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