Hydrochloric Acid → HCID 178486758, compound

HRID 445468Notes

Reaction equation

HRID 445468 reaction equation
[O-][CH2:2]C.[Na+].[NH2:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]([O:20][CH3:21])=[CH:8][C:7]=1[C:22](=[O:24])[CH3:23].C(OCC)=O.Cl>COCCOC.O>[CH2:13]([O:12][C:10]1[CH:11]=[C:6]2[C:7]([C:22]([OH:24])=[CH:23][CH:2]=[N:5]2)=[CH:8][C:9]=1[O:20][CH3:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 2723922Sodium ethoxide2×HCID 226671471-(2-Amino-4-(benzyloxy)-5-methoxyphenyl)ethanone

Product 1

HCID 178486758HCID 178486758, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium ethoxide (74.8 g, 1.1 mol) was added to a solution of 1-(2-amino-4-benzyloxy-5-methoxyphenyl)ethanone (29.3 g, 108 mmol) in DME (700 mL) and stirred for 30 min. Ethyl formate (44 mL, 540 mmol) was added and the mixture was stirred overnight (in case of incomplete reaction, additional sodium ethoxide can be added and the reaction monitored by LC/MS). After the reaction was complete, the mixture was diluted with water (40 mL) and acidified to neutral pH with 1M HCl. The solid was filtered, washed with water and dried to afford 7-benzyloxy-6-methoxyquinolin-4-ol (22 g, 72%). 1H NMR (400 MHz, CDCl3): δ 10.7 (br s, 1H), 7.70 (s, 1H), 7.49-7.46 (t, 1H), 7.43-7.41 (br d, 2H), 7.37-7.33 (t, 2H), 7.30-7.28 (d, 1H), 6.84 (s, 1H), 6.21-6.19 (d, 1H), 5.21 (s, 2H), 3.96 (s, 3H). LC/MS (M+H=282).

Workup

  1. stirringthe mixture was stirred overnight (
  2. additioncan be added
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-10a4f52c565f43579cabea06b2d425bb
Source dataset
uspto-grants-2013_07
Patent number
US08476298B2

Reaction notes

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