Hydrochloric Acid → HCID 178486758、化合物

HRID 445468

反応式

HRID 445468 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 178486758HCID 178486758、化合物収率 72.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-10a4f52c565f43579cabea06b2d425bb
出典データセット
uspto-grants-2013_07
特許番号
US08476298B2

関連ノート

読み込み中…