Triethylamine → HCID 67263649, compound

HRID 1688134Notes

Reaction equation

HRID 1688134 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[NH2:12].C(N(CC)CC)C.Br[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>C1COCC1>[C:25]([O:24][C:22](=[O:23])[CH2:21][NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[NH2:12])([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 578538082-(Aminomethyl)-5-nitroaniline

Product 1

HCID 67263649HCID 67263649, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-aminomethyl-5-nitro-phenylamine (2.84 g, 17 mmol) in dry THF (150 mL) and triethylamine (12 mL, 85 mmol) was added tert-butyl bromoacetate (5 mL, 34 mmol). The mixture solution was stirred at room temperature for 16 hours and concentrated. Chromatography of the resulting residue on silica gel with methylene chloride and methanol (50:1) gave 2.15 g of (2-amino-4-nitro-benzylamino)-acetic acid tert-butyl ester (45%): 1H NMR (300 MHz, CDCl3) δ 7.58 (dd, 1H), 7.55 (5, 1H), 7.22 (d, 1H), 5.2 (br, 2H) 3.95 (s, 2H), 3.39 (s, 2H), 1.58 (s, 9H); MS (m/e): 282.3 (M+1).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-227a0170c5214cd799cf54843be77788
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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