Hydrochloric Acid → 4-(2-Aminobenzyl)phthalic acid dimethyl ester

HRID 1357384Notes

Reaction equation

HRID 1357384 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:30])[C:5]1[C:6](=[CH:11][C:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH:22]C(OC(C)(C)C)=O)=[CH:13][CH:14]=1)[C:7]([O:9][CH3:10])=[O:8]>C(OCC)C.CO>[CH3:2][O:3][C:4](=[O:30])[C:5]1[C:6](=[CH:11][C:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH2:22])=[CH:13][CH:14]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 699938044-(2-(Tert-butoxycarbonylamino)benzyl)phthalic acid dimethyl ester

Product 1

HCID 699958444-(2-Aminobenzyl)phthalic acid dimethyl esterYield 92.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

2N hydrogen chloride in diethyl ether (1 ml) was added to a solution of 4-(2-(tert-butoxycarbonylamino)benzyl)phthalic acid dimethyl ester (100 mg, 0.25 mmol) in methanol (1 ml). The mixture was stirred for 2 hours at room temperature and evaporated to dryness in vacuo. The crude product was recrystallized from diethyl ether/ethyl acetate to give light, golden crystals of 4-(2-aminobenzyl)phthalic acid dimethyl ester (yield: 69 mg (86%)). 1H—NMR (CDCl3) in ppm: δ 7.74 (1H,d); 7.60 (1H,s); 7.54 (1H,d); 7.27 (2H,d); 7.13 (1H,m); 7.05 (1H,d); 4.12 (2H,s); 3.8 (6H,2xs); 2.5 (3H,s). LC-MS: m/e 322 (M+Na), 300 (MH+).

Workup

  1. customevaporated to dryness in vacuo
  2. customThe crude product was recrystallized from diethyl ether/ethyl acetate

Sources & evidence

ORD record
ord-fbaffe81925540db8dd2aae63062a4b8
Source dataset
uspto-grants-2003_07
Patent number
US06590118B1

Reaction notes

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