Diisopropylethylamine → (3-Bromo-2-nitro-phenylamino)-acetic acid ethyl ester

HRID 1056027Notes

Reaction equation

HRID 1056027 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[C:3]=1[N+:9]([O-:11])=[O:10].Cl.[NH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(N(C(C)C)C(C)C)C>CC(N(C)C)=O.C(Cl)Cl>[Br:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([NH:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 27831521-Bromo-3-fluoro-2-nitrobenzene

Product 1

HCID 59392671(3-Bromo-2-nitro-phenylamino)-acetic acid ethyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of 1-bromo-3-fluoro-2-nitrobenzene (10.25 g, 46.6 mmol; Ark Pharm, Inc., Libertyville, Ill.), ethyl 2-aminoacetate hydrochloride (6.50 g, 46.6 mmol; Aldrich), and N-ethyl-N-isopropylpropan-2-amine (24.35 ml, 140 mmol) in DMA (116 ml) was heated to 80° C. for 5 h. The mixture was diluted with DCM (400 ml), added to a separatory funnel, and washed with water (4×200 ml) before the organic layer was separated, dried over Na2SO4, and concentrated to give ethyl 2-((3-bromo-2-nitrophenyl)amino)acetate (210b, >99% yield) as a yellow oil (contaminated with DMA). MS (ESI, pos. ion) m/z: 303.0/305.0 (M+1).

Workup

  1. additionadded to a separatory funnel
  2. washwashed with water (4×200 ml) before the organic layer
  3. customwas separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b5bd9471cec24f07956eb8aad66c1470
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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