Hydrochloric Acid → HCID 54077828, compound

HRID 844131Notes

Reaction equation

HRID 844131 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[NH2:12][C@H:13]([C:15]([OH:17])=[O:16])[CH3:14].C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:12][C@H:13]([C:15]([OH:17])=[O:16])[CH3:14])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 11430Potassium CarbonateHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 54077828HCID 54077828, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 4-bromo-2-fluoro-1-nitro-benzene (22 g, 100 mmol), L-alanine (8.9 g, 100 mmol), and potassium carbonate (17.5 g, 125 mmol) in ethanol (250 ml), and water (200 ml) was heated to reflux for 5 hours. After cooling to room temperature, the mixture was diluted with water, and acidified with 1N hydrochloric acid. The precipitate was collected on a funnel and dried to afford N-(5-bromo-2-nitrophenyl)-alanine (28.9 g, 100%). A sample was recrystallized from ethanol: m.p. 183-187° C.; 1H-NMR (DMSO-d6) δ1.44 (d, J=6.9 Hz, 3H), 4.56 (m, 1H), 6.87 (d, J=6 Hz, 1H), 7.21 (d, J=1.7 Hz, 1H), 7.99 (d, J=7 Hz, 1H), 8.36 (d, J=7 Hz, 1H), 13.27 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours
  3. customThe precipitate was collected on a funnel
  4. customdried

Sources & evidence

ORD record
ord-01c89ccb67774e60a31192730c251be6
Source dataset
uspto-grants-2002_04
Patent number
US06380235B1

Reaction notes

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