Hydrochloric Acid → HCID 178471686, compound

HRID 40824Notes

Reaction equation

[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.Cl.[C:18]1([O:24]C2C=CC=CC=2)C=C[CH:21]=[CH:20][CH:19]=1>>[CH2:13]([O:12][C:10]([CH2:9][CH2:8][CH2:7][O:6][C:5]1[CH:4]=[C:3]2[C:2](=[CH:16][CH:15]=1)[N:1]=[C:20]([CH3:21])[CH:19]=[C:18]2[OH:24])=[O:11])[CH3:14]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 7583Diphenyl Ether

HCID 14451766Ethyl 4-(4-aminophenoxy)butanoate

Product 1

HCID 178471686HCID 178471686, compoundYield 42%

Procedure

To a stirring mixture of ethyl 4-(4-aminophenoxy)butanoate (3.12 g, 14 mmol) and acetoacetic ester (1.82 g, 14 mmol) was added a catalytic amount of hydrochloric acid and cyclized in refluxing diphenyl ether as described in Example 5a. The product was obtained as a light yellow solid (1.70 g, 42%). 1H NMR (400 MHz, DMSO-d6): 1.32 (3H, t, J=7.1 Hz), 2.15 (2H, m), 2.50 (3H, s), 2.62 (2H, t, J=7.3 Hz), 4.21 (4H, m), 6.09 (1H, s), 7.42 (1H, dd, J=9.0, 2.7 Hz), 7.58 (1H, d, J=2.7 Hz), 7.65 (1H, d, J=9.0 Hz), 11.8 (1H, s).

Sources & evidence

ORD record: ord-a542f66eae854ddfb5cd6f103536733e
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530491B2

Reaction notes

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