Methanimidamide, hydrochloride (1:1) → HCID 178486770, compound

HRID 871309Notes

Reaction equation

HRID 871309 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][Cl:15])=[CH:6][C:5]=1[NH2:16].Cl.[CH:19](N)=[NH:20]>C(O)C>[Cl:15][CH2:14][CH2:13][O:12][C:7]1[CH:6]=[C:5]2[C:4]([C:3]([OH:2])=[N:20][CH:19]=[N:16]2)=[CH:9][C:8]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 10313058Methanimidamide, hydrochloride (1:1)HCID 23033001Methyl 2-amino-4-(2-chloroethoxy)-5-methoxybenzoate

Product 1

HCID 178486770HCID 178486770, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 2-amino-4-(2-chloro-ethoxy)-5-methoxy-benzoic acid methyl ester (2.4 g, 9.24 mmol) in ethanol was added formamidine hydrochloride (2.97 g, 36.96 mmol). The mixture was heated at 130° C. in sealed tube for 8 h. The precipitate formed was filtered and washed with ethanol and dried to afford the pure compound 7-(2-chloro-ethoxy)-6-methoxy-quinazolin-4-ol (2.25 g, 96%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 7.95 (s, 1H), 7.45 (s, 2H), 7.15 (s, 1H), 4.40 (t, 2H), 4.00 (t, 2H), 3.88 (s, 3H), LC-MS (ESI) m/z 255 (M+H)+.

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-0f17d338ab3b40f8bbecae933e58d032
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

Loading…