Hydrochloric Acid → HCID 81445331, compound

HRID 514439Notes

Reaction equation

HRID 514439 reaction equation
N([O-])=O.[Na+].S(=O)(=O)(O)O.N[C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[CH2:21][CH3:22])[C:14]([O:16][CH3:17])=[O:15].[ClH:23]>C(O)(=O)C.Cl[Cu]>[Cl:23][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[CH2:21][CH3:22])[C:14]([O:16][CH3:17])=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 13399999Methyl 3-amino-4-ethylbenzoateHCID 23668193Sodium Nitrite

Product 1

HCID 81445331HCID 81445331, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
5 °C

Procedure

Charge NaNO2 (579 mg, 8.37 mmol) and concentrated sulfuric acid (6 mL) to a flask. As methyl 3-amino-4-ethylbenzoate (1.37 g, 7.62 mmol, PREPARATION 5) in acetic acid (18 mL) was added at 0° C., color of the mixture turned to yellow, and then stirred at 5° C. for 1.5 h. The solution above was added to a dark mixture of CuCl (1.65 g, 16.65 mmol) in concentrated HCl (18 mL) slowly at 0° C., stirred for 2 h, and poured into ice water, extracted with DCM, the organic phase was concentrated to give 582 mg of the title compound (38%). 1H NMR (400 MHz, CDCl3): δ 1.25 (3H, t, J=8.0 Hz), 2.80 (2H, q, J=7.6 Hz), 3.91 (3H, s), 7.30 (1H, d, J=7.6 Hz), 7.85 (1H, dd, J=1.2, 7.6 Hz), 8.01 (1H, d, J=1.6 Hz).

Workup

  1. stirringstirred for 2 h
  2. extractionextracted with DCM
  3. concentrationthe organic phase was concentrated

Sources & evidence

ORD record
ord-b4e929ce12684b42bf34fe93a29bb444
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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