1,2-Dichloroethane → 7-Nitro-1H-indole-2-carboxylic acid (2-chloro-ethyl)-amide

HRID 1045862Notes

Reaction equation

HRID 1045862 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([OH:15])=O)=[CH:9]2)([O-:3])=[O:2].C(N(CC)CC)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[Cl:37][CH2:38][CH2:39][NH2:40].Cl>CN(C)C=O>[Cl:37][CH2:38][CH2:39][NH:40][C:13]([C:10]1[NH:11][C:12]2[C:8]([CH:9]=1)=[CH:7][CH:6]=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2])=[O:15]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 133692-ChloroethylamineHCID 757711-HydroxybenzotriazoleHCID 814097-nitro-1H-indole-2-carboxylic acid

Product 1

HCID 866443587-Nitro-1H-indole-2-carboxylic acid (2-chloro-ethyl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Nitro-1H-indole-2-carboxylic acid (371 mg, 3.2 mmol) prepared in Step A was dissolved in N,N-dimethylformamide (10 mL). Triethylamine (0.6 mL, 4.3 mmol), EDC (614 mg, 3.2 mmol) and HOBT (433 mg, 3.2 mmol) were added, 2-chloroethylamine (252.8 mg, 3.2 mmol) was added, and the mixture was stirred for 8 h at room temperature. 1N-hydrochloric acid solution was added, and the reaction mixture was extracted with ethyl acetate, washed with saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure to give the title compound.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationThe filtrate was distilled under reduced pressure

Sources & evidence

ORD record
ord-8ec3b31491f249b288c1f6140276b73a
Source dataset
uspto-grants-2013_10
Patent number
US08569307B2

Reaction notes

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