Hydrochloric Acid → HCID 178486758, 화합물

HRID 445468노트

반응식

HRID 445468 반응식
[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

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 2723922Sodium ethoxide2회HCID 226671471-(2-Amino-4-(benzyloxy)-5-methoxyphenyl)ethanone

생성물 1

HCID 178486758HCID 178486758, 화합물수율 72.4%

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-10a4f52c565f43579cabea06b2d425bb
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476298B2

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